Author Topic: Mercuric/aluminum amalgam reduction of substituted Beta-nitrostyrenes to amines  (Read 599 times)

poisoninthestain

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Mercuric/aluminum amalgam reduction of substituted Beta-nitrostyrenes to amines
« on: April 01, 2009, 08:28:13 PM »
approx. double the amount nitroalkene of Heavy Duty, non-stick aluminum foil is cut into/paper shredded(easier of the two) ~1x1cm squares. Then the cut foil is added to a blender and allowed to be chopped for a minute or so. This allows the outer coating of aluminum oxide to be chipped off and exposes the elemental aluminum underneath so the mercuric salt can stick to it thus preventing more aluminum oxide from forming.

Now we need to prepare the nitrostyrene for the amalgam. Mix 10x foil amount GAA + 8x IPA + your nitrostyrene(which should be half the amount of foil). It needs to be incubated until the solution is fairly hot(not boiling!) for everything to dissolve so it pours nicely into your amalgamation flask. Why can't you just dump the powder in? Well, solvating the styrene in GAA and IPA makes it react more evenly and efficiently because it's ionized which will work perfect for the hydrogen being produced on the aluminum.

The previously chopped foil is added to a large flask(at least 1000ml) to prevent overflow(and it'll foam like hell trust me). Now to this add a dash of any mercuric salt(I used HgCl2 because of it's high solubility), then 4x the amount of foil of either IPA, ethanol or methanol(methanol has a higher solubility so I used MeOH) and same proportion(4x) of dH2O. Ex: 40ml MeOH + 40ml dH2O.

At this point the amalgam is ready. Let it sit somewhere for 15-30 minutes. By this point in time you should see little hydrogen bubbles. This means the amalgam is successful and the hydrogen reduction is occuring where the foil meets the solvent(the alcohol). When the bubbles start to occur very rapidly dump in the prepared styrene solution all at once. This will insure everything reacts uniformly.

The whole reduction takes  ~30-60min from start to end. The color should start from a yellow/orange->green/yellow->black/grey. If this is your situation then the reduction was most likely successful. Unreacted styrene's refraction index is green which means it didn't make it all the way. If this happens to you and your solution is still green add another dash of mercuric salt and wait for the rxn as before. Once everything slows down to a halt and no more hydrogen evolution is present prepare a 25% KOH/NaOH solution and add it to the post-reduction flask.

This will basify the reacted aluminum(and also strongly exothermic) into aluminum hydroxide and the acetic acid into NaAc making the solution now MUCH easier to filter. This will also form the freebase of your amine. One way to tell if your reduction was successful is if two phases form: the upper should be light, and the bottom should be dark. Whip out the buchner and prepare to use quite a few filter paper disks. Hook the buchner to a vac pump(the hand pump takes forever) and pour in portions of the rxn flask. You're going to have to change the filter paper when it cakes over into a grey/black sludge. It's a good idea to double stack filter paper as they seem to last longer this way and filter better. After vac filtering your filtrate should not be dark at all. Mine was always a very light color but your amine color may vary.

Once the filtrate is isolated, A/B extract as usual to obtain the freebase or salt. The pic of the sep funnel with a lower yellow phase is the amine freebase post-workup solvated in DCM.

-PStain.
« Last Edit: April 01, 2009, 08:40:27 PM by poisoninthestain »

poisoninthestain

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Re: Mercuric/aluminum amalgam reduction of substituted Beta-nitrostyrenes to amines
« Reply #1 on: April 01, 2009, 09:15:20 PM »
I should also add I always write my writeups with scaling in mind. Since I suck at molarity(and math in general). If you scale this up to 20g nitrostyrene you better be prepared to use a 3000ml flask or a pickle jark. Seriously, the foam is monsterous.

Did I mention the alcohol solution is mad poisonous? Don't fuck with it. Wear non-permeable gloves at the very least. I'm a pussy and I wear a gas mask, long sleeves, goggles...the whole deal.

Also you're going to have to dispose of the mercuric sludge somehow. The thing is you CAN'T add too much mercuric salt. If you over-amalgamate it reduces to elemental mercury. So now comes the question that is up to much debate...what to do with the sludge? Well, I personally dump most of my trash outside...deep deep deep in the woods far away from civilization. Or you can dump it down the toilet and have many people hate you. Doesn't matter.

Interesting side-note, I spoke with someone who worked at a water-treatment plant about this and he said "seriously it's no big deal...we have filters so strong they can rip your bones off"...i'll take his word for it.

Anyways, in the future I'll probably follow this up with halogenating an amine or something, or an allylbenzene to a ketone and then ketone to an amine. I just wish I had some more cash to finance my adventures *sigh*.

poisoninthestain

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Re: Mercuric/aluminum amalgam reduction of substituted Beta-nitrostyrenes to amines
« Reply #2 on: April 01, 2009, 10:04:44 PM »
One more thing. After the amalgam is all pooped out you'll notice that light-colored top phase, right? Well, don't titrate without filtering. Or better yet don't titrate at all unless you feel extremely confident. I decided to experiment once that way and I ruined a whole bunch of amine  :-[ ...

If you titrate with HCl you'll form the amine salt and a whole slew of other trash. It won't even matter if the PH is ~3-4 just to pull the amine salt. The reduction sludge is truely your buchner's worst nightmare.

Also you're probably going to want to do this outside. It'll get really hot! This will cause hydrogen evolution(yay hydrogen!) and alcohol fumes(boo alcohol fumes!) ...IPA and ethanol really aren't a problem and you could do them inside if you feel really confident in your foam control skills, but if using methanol I'd opt for doing it outside. Methanol doesn't really have a smell, a weak ethanol scent at the very least. Skin contact with it actually is very non-toxic but inhalation and especially eye contact(obviously ingestion) are extremely bad. The metabolites are formic acid and something else which escapes me...

Anyways, be safe. The only reason I know this is because I'm a hypochondriac and read way to many MSDS's for my own good.   :D

Vesp

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Re: Mercuric/aluminum amalgam reduction of substituted Beta-nitrostyrenes to amines
« Reply #3 on: April 01, 2009, 10:20:34 PM »
very nice write up!
Its is very important to be safe when dealing with these types of chemicals.  Hg, and its compounds are very scary when it comes to their toxicity and what they do to you. This is probably why I haven't messed with the lovely amount of Hg I've obtained.  The methanol is metabolized into formaldehyde, and then to formic acid I believe.
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poisoninthestain

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Re: Mercuric/aluminum amalgam reduction of substituted Beta-nitrostyrenes to amines
« Reply #4 on: April 01, 2009, 11:59:24 PM »
I forgot to mention a lil tid bit that I find useful. I've often asked myself "how much of a 25% solution is enough?"...such as the example where you basify the amalgam.

Well, here's how I do it. Determine the total amount of milliliters in the given rxn, take half of that(which will be the amount of KOH/NaOH), and then make that amount the 25% by diluting it with water(75%).

Ex: 1000ml reagents -500ml = 500ml base + 75% water(1500ml) = 25% solution

I noticed that this scheme usually doesn't leave any room for unreacted reagents and dissolves everything pretty clean.
« Last Edit: April 02, 2009, 12:01:05 AM by poisoninthestain »

Sedit

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Re: Mercuric/aluminum amalgam reduction of substituted Beta-nitrostyrenes to amines
« Reply #5 on: April 02, 2009, 07:33:04 PM »
Sorry its a little off topic but Poison since you appear to have the means to do so would you be interested in testing a replacement for Mercury chloride?

Its a mixture of CuSO4 and NaCl that breaks though the passification of the Al in the same manner as Hg2Cl2. I attempted it using MeNO3 and the smell of methylamine was wonderfuly present but im woundering if it will perform the same on styrens which I believe it will. How nice would it be to have nothing more to deal with but a salt water solution.

Cool pics also. Nice. :)
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poisoninthestain

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Re: Mercuric/aluminum amalgam reduction of substituted Beta-nitrostyrenes to amines
« Reply #6 on: April 02, 2009, 08:49:16 PM »
Hey sedit. Nice to see you again.

Sure I'd be more than willing to give it a shot. I've been working on so much recently my head's going to melt so it'd be some time in the future that'd I'd get the opportunity to attempt it.

You'd have to fill me in on the details such as references, texts, ect. beforehand. I never heard of CuSO4 and NaCl being used that way EVER. Sounds pretty novel. I like the idea a lot.

This reduction also works on *most* phenyl-2-nitropropenes as well. But anyways, I'm about 80% sure your method will work flawlessly on nitrostyrenes also.

My reasoning is this: CuSO4 and NaCl are both inorganic salts much like HgCl2. If they can cut past the aluminum oxide then that's pretty much all that matters as long as they don't bond with the compound you're trying to reduce.

It's the elemental aluminum that has to make it through the reaction. All else is really trivial. If it'll work for a ketone it'll work for a nitroalkene. So me thinks.
« Last Edit: April 02, 2009, 08:52:20 PM by poisoninthestain »

Vesp

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Re: Mercuric/aluminum amalgam reduction of substituted Beta-nitrostyrenes to amines
« Reply #7 on: April 02, 2009, 09:37:20 PM »
Interesting to hear about this possible reaction. How does this reaction work? I'm assuming that elemental copper must form in the end. Is it actually the mix of CuSO4 an NaCl that matter, or would CuCl2 work? Na2SO4 + CuCl2 would make the same solution, and I have a hard time seeing any way in which the NaCl or Na2SO4 would play a roll in this reaction.

Wow it would be too amazing if this worked!
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Sedit

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Re: Mercuric/aluminum amalgam reduction of substituted Beta-nitrostyrenes to amines
« Reply #8 on: April 03, 2009, 01:04:39 AM »
Has to be the mixture.

You can make a solution of CuSO4 and add Al with almost no reaction just faint bubbles and slight darkening and yet a pinch of NaCl it errupts into hell fire precipitating Fine Cu. Ill see what I can pull up for you about it. When I tryed it with MeNO3 it was just on a whim because I had some CuSO4 from electrolyis I was performing and thought what the hell Iv seen reports of others getting the MeNH3 from it..(ill post them later) and damn if it dont sure smell like it.

It was Klute I believe that I first heard this reaction from and honestly I dont exactly know whats going on besides that I think The -Cl ion is behaving like CuCl solution but im not sure. Ill look into it and see what I can find.

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poisoninthestain

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Re: Mercuric/aluminum amalgam reduction of substituted Beta-nitrostyrenes to amines
« Reply #9 on: April 03, 2009, 02:43:13 AM »
Correct me if I'm wrong but doesn't NaCl make water a better conductor of electricity?

I don't know shit about electrolysis is why I ask.

I'm gonna take an educated guess and say that the NaCl acts as a catalyst while the CuSO4 functions as the actual amalgam by forming an alloy on the aluminum. This would explain how the HgCl2(or other mercuric salts for that matter) functions as both, the alloy and the catalyst.

The proof we know it's a catalyst is because technically it isn't consumed by the rxn and can *possibly* be regenerated(who would want to anyways). Also, this is outright proof of the toxicity of the mercuric alcohol solution. If the Hg salt were consumed there wouldn't be the great risk associated with the reduction(although elemental Hg would still be present).

A further point in my theory on how this works is that you said you saw elemental Copper precipitate as the reduction was running. This is exactly the same reduction experienced by HgCl2 into Hg metal.

Bottom line: NaCl gives the CuSO4 the boost to amalgamate. It all has to do with electronegativities me thinks.

Vesp

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Re: Mercuric/aluminum amalgam reduction of substituted Beta-nitrostyrenes to amines
« Reply #10 on: April 03, 2009, 11:25:19 PM »
poisoninthestain.. that was a confusing post.  How does electrolysis matter here? Anything that ionizes in water acts as a conductor so all salts that are soluble to some extent increase water's conductivity.

I highly doubt you could ever get Sodium Chloride back with out totally changing everything in there.

Sodium chloride and copper sulfate both ionize in solution, you'd likely only be able to recover sodium sulfate and copper chloride since sodium sulfate is a more favored product then sodium chloride.

This is why I was asking if copper chloride could be used instead of the combination. If you could use just copper sulfate/chloride with hydrochloric acid this may be better (or worse) because when a salt is dissolved in an acid, it can prevent it from ionizing as much and would slow down the reaction. This is known as the common-ion affect. I think it may be beneficial in some way if it is good to react faster,  but knowing this would also help if you wanted it to react slower for whatever reason, you could simply just add more salt to the solution.

I know there is another mercury substitute - it is some alloy similiar to woods metal, and it melts at a very low temperature and is able to take off the oxide layer. I don't know if i can locate where I've read about it though. 

Sedit, perhaps you may want to try reducing MeNO3 with just HCl and Al, because it seems like that might work as well, and then it would point you in the right direction. Things like nitrobenzene to aniline don't need Hg to be reduced.
« Last Edit: April 03, 2009, 11:27:00 PM by Vesp »
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treg

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Re: Mercuric/aluminum amalgam reduction of substituted Beta-nitrostyrenes to amines
« Reply #11 on: April 04, 2009, 02:21:25 AM »
Excellent discussion of amalgam reductions, thanks! Good to see you poisoninthestain and sedit as well, tregar here. Nice to meet you Vesp.

Poisoninthestain said:
"Heavy Duty, non-stick aluminum foil is cut into/paper shredded(easier of the two) ~1x1cm squares. Then the cut foil is added to a blender and allowed to be chopped for a minute or so. This allows the outer coating of aluminum oxide to be chipped off and exposes the elemental aluminum underneath so the mercuric salt can stick to it thus preventing more aluminum oxide from forming."

The shredder, the blender, incubation heat...3 excellent points, thanks again.

When a micro amalgam was tried without using a shredder, blender, or incubation, did not get beyond "warm" .... these excellent pointers should help to get hot, steaming, and going.
« Last Edit: April 04, 2009, 02:30:24 AM by treg »

Sedit

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Re: Mercuric/aluminum amalgam reduction of substituted Beta-nitrostyrenes to amines
« Reply #12 on: April 04, 2009, 05:53:06 AM »
Welcome Treg
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poisoninthestain

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Re: Mercuric/aluminum amalgam reduction of substituted Beta-nitrostyrenes to amines
« Reply #13 on: April 04, 2009, 12:28:39 PM »
Vesp- sorry bout the confusion. I was referring to Sedit's point about something involving electrolysis. I really don't know crap about anything electrical so I'm just guessing.

Sedit

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Re: Mercuric/aluminum amalgam reduction of substituted Beta-nitrostyrenes to amines
« Reply #14 on: April 04, 2009, 02:10:47 PM »
    Sorry electrolysis was just  referring to the means that I generated the CuSO4. If you know nothing about electrolysis poison you should look into it. Its a vary useful hands off way of generating so many in organic salts its unreal. Intimate knowlage isnt needed just a basic grasp of whats what and then you can start to explore divided cells, Mercury cathodes(instant ability to generate Sodium amalgam from NaCl) and gas phase reactors ect. So much can be done with it that its only a matter of time that most synthesis take place in such reactors.

ECS website:
http://www.ecsdl.org/vsearch/servlet/VerityServ
let?KEY=ECSLIB&ONLINE=&CURRENT=&smode=freesearch&fromvolume=&tovolume=&fromissue=&toissue=

Decent place to find some more up to date advanced techniques.
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poisoninthestain

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Re: Mercuric/aluminum amalgam reduction of substituted Beta-nitrostyrenes to amines
« Reply #15 on: April 04, 2009, 03:47:44 PM »
Yeah, I really should take a peek into it. I've only heard great things about it. If you have any good beginner references or anything just PM me.

poisoninthestain

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Re: Mercuric/aluminum amalgam reduction of substituted Beta-nitrostyrenes to amines
« Reply #16 on: April 04, 2009, 08:10:55 PM »
Sedit- I've aquired some CuSO4 OTC from root killer(95% purity), would iodized NaCl table salt suffice as well?

Also, give me the ratios. I'm willing to sacrifice 5g nitrostyrene attempting this.

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Re: Mercuric/aluminum amalgam reduction of substituted Beta-nitrostyrenes to amines
« Reply #17 on: April 04, 2009, 09:38:40 PM »
Just a few things I could pull up for you quickly, Im having a very busy day and Ill give ya some more later if time permits..


Here is a link to woelens site that inspired bio which inspired Klute ect..ect... Anyhoo...

http://woelen.scheikunde.net/science/chem/exps/cu+al/index.html


A fine discription of the reaction.

Quote
Aluminum reacts vigorously with water, when its passivating layer of oxide is effectively destroyed. This can be achieved by using tetrachloro or tetrabromo complexes of copper (II).
Acid can also be used to destroy the passivating layer, but this takes considerably more time.
Cobalt has a similar effect as copper (II), but it is less pronounced.


And some quick reading material... This is the first test performed by Klute

Quote
I've FINALLY manadged to run a few tests... and the news are good...

About half a mL of a sat. fresh CuSO4 solution was introduced in a test tube, followed by enough sat. NaCl solution to cause a change in color, from nice deep CuSO4 blue to a light green/Feso4-style color. Then about 0.1 of shredded Al was added. After only a few seconds, light bubbling started, with the apparition of some black deposit. After perhaps a minute, the solution had turned transparent, the AL was bubbling (very fine bubbles, much less vigorous than an AL/Hg) and there was some voluminious black and dark brick-red deposits, by spots. They looked like mold. It wasn't a layer of the stuff, just some dark spots. The test tube had heated up to be warm on touch, about 30-35°C. Then about 0.5ml of pur Nitromethane was added, and the test tube shaked constantly. When shaking was stopped, the nitro seperated as a clear layer on top. The Al was already starting to decompose in grey sludge. The tube was shaked regulary for about 5-7 minutes. The nitro layer seemed to dimish, and the test tube seems to heat up more and the bubbling was more vigorous. This could just have been because the reaction with water was kicking in. No smell above the test tube, but as the CuSO4 was acidic (H2SO4 from preparetion), the possibly formed MeNH2 would be as a salt. It was left as is, shaken every minute or so, while another test tube was prepared.
The complex was prepared as in the first test, using roughtly the same amount. Al was introduced, and left to fizz until the solution had turned transparent. Again, the same black and dark red deposits. After 5 minutes with occasional shaking, the solution was decanted off, and 0.5mL of MeNO2 added. This covered the Al. To my releif, bubbling continued, slowly, gently. Some sludge started appearing, but didn't dissolve in the nitro, so the Al/black and red deposits/ sludge form a semi solid mass stuck to the bottom of the tube. Bubbles were evolving from every part of the Al. This tube was definitively hotter than the other one, but didn't bubble more violently.

A third test tube was prepared, using 2x the amount of Cu2+ and Cl- to prepare the complexe, but the same amount of Al. It was left as is, with occasional shaking.

Some 40% NaOh was added to the first test tube. The reaction had nearly died down altough there was alot of Al left, and a little nitro. There was alot of grey sludge. As soon as the base was added, the Al started bubbling and decomposing. No MeNH2 smell. After a few minutes, bubbling was violent, and the grey sludge turned dark green colour, you know that yucky sewer color. But, then, eureka, MeNH2 smell! It smelled just like a finish Al/Hg, although less stronger...

The second test tube was still slowly reacting, but bubbling a lot less. The nitro layer had dimished, and still no smell of MeNH2. Alot of grey sludge had evolved. Some more Cu2+ and Cl- solution was added, to see what the complexe would do on any formed amine (Seeing the smell in the first tube, i was sure it had worked here too, if not better.) The solution turned dark green/yellow, a bit like a old curry sauce or something, and the bubbling speeded up a little. After a minute, NaOH solution added. The Al started decomposing, no MeNH2 smell but another strange unplesant smell. Even after 5 mintues, there was still this unpleasant smell, and no amine.

In the third tube, there was much more deposits then the other, the solution had clared up.

Conclusions:

The Al is "activated" in such to be able to reduce compounds like MeNO2, although the reaction seems to be very slow. Apparently, the presence of water from the complex solution doesn't seem to prevent such reductions. But, for any quantitative transformations, more experiences need to be done.

The [Cu(Cl)4]2- is turned into some strange compound of the surface of the Al as dark-red spots. It doesn't look like metallic Cu IMHO. Not at all shiny, and dark bric-red color. Black spots are also present, although this *could* be a impurity in the Al that reacts. The AL used leaves nothing after reaction with 50% NaOH (no visible Fe, Cu, Sn, etc). The fact that the green color disappears after a few minutes and these deposits appears proves so. Also adding more complex forms more deposits. So the Cu cannot form complexes with formed or added amines for example. The fact that MeNH2 is smelled when no complex is added after is formation, but no smell is apparent when more complex is added suggests this. But, as the second reaction was run with much less water, it isn't possible to affirm the absence of MeNH2 smell was entirely du to the complex addition.

Adding more complex *seems* to quicken the reaction, but causes more deposists that cover the Al surface. Apparently, seeing that the reactions continues when the complex solution is decanted when discolred, the "activation" is catalytic, and not stoechiometric. And the Al decomposes to Al(OH)3 as in an Al/Hg and doesn't passivate again.

So, I think that with more work and experiemnts, this complexe could be used to replace Hg salts in Al reductions. Although it isn't sure that it could reduces imines and such, and specific reaction conditions need to be found.
As for now I personaly don't have much avalible time, and other interests, I'll surely won't continue researching into this at the moment. I greatlt encourage other people interested to do so, it could be a great change, and avoid alot of people using toxic Hg salts.. And even if alot reagents and time are spent into this, that's were they are the best spent! Imagine if reductions could simply be done with AL, Cu and salt!

Ill see what I can dig up for you later gotta go now.
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Vesp

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Re: Mercuric/aluminum amalgam reduction of substituted Beta-nitrostyrenes to amines
« Reply #18 on: April 05, 2009, 12:51:49 AM »
wow awesome! this is exciting!
I can't wait to hear your results from this poisoninthestain!

thanks for the info sedit! I'll look for more later when I get the chance. woelens page helped me understand what is going on a lot more.
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poisoninthestain

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Re: Mercuric/aluminum amalgam reduction of substituted Beta-nitrostyrenes to amines
« Reply #19 on: April 05, 2009, 01:20:15 AM »
Beautiful info Sedit. I really absorbed it.

So how's this sound...I follow my writeup exactly as below subbing in 5g nitrostyrene and adding a dash of NaCl for HgCl2 and adding small portions of CuSO4 until the rxn starts to produce hydrogen evolution?

I have a few questions though. If I use methanol as my solvent will that produce dimethyl sulfate somehow from the SO4 ions in the solution?  :o I don't think it would, just wanna make sure.

Also, the only difference from the methylamine reduction as far as I can tell is that it's base-catalyzed, while the nitrostyrenes(and nitropropenes) are acid-catalyzed which is why I used GAA in my writeup as the catalyst. IceCool talks about this in great deal if you can find his posts lingering on the net, might be on WD under MD-series questions or something.

I have almost no doubt this won't work. I can't wait. Too bad I broke my sep. funnel today from not greasing the fucking joints.  >:(

ARGGG!