Same story again.
Feel like complete moron.

Tripple checked molar ratios and everything.
Waited for amalgamation full 15 min at 23,5°C r.t. until it became totaly cloudy,Al dull and many bubbles coming out.
Added oxime,some kind of reaction started.
Added GAA...catastrophe!
All bubbles dissapeared,all aluminum sank,no signs of life for 30 min.
Tried to measure pH,it was somewhere between 3-5.
Added even more GAA...nothin.
THEN!
Added roughly the same molar ratio of NaHCO3 as GAA.
Some eferescence started,added much more MeOH (to compensate
decrease of oxime solubility that water liberated in neutralization created)
Stirring became allmost imposible,a lot of salt is created BUT!!!

There seems to be reaction going,at least slowly.
I will leave it like that until tomorow and tell you guys more tommorow.

So,GAA definitely killed reaction.
I can't understand how people have any sucess with that crap inside rxn!!!
What about Chromics method that used no acid and got decent yields!?

There is nothing more frustrating than having high purity precursors and p.a. grade chemicals
but still failing when you do everything right!

Bizarre. I've never encountered this problem before, nor has anyone else I've been in touch with. I used to wait until the amalgamation is well under way before adding the rest of the reagents, thats one of the reasons such a large XS of Al is used. It looks like its boiling, but really its a lot of hydrogen evolution, so don't be shy crank it up! You can always add more amalgum later in the rxn. Also didn't see that you heated the rxn as per the write up, it well help.

I usually have my rxn vessel sitting inside a big plastic bin on the stir plate so if things get out of hand I can simply dump some ice water in the bin to cool things off, you can even do this towards the end when the rxn is very thick and the hydrogen evolution threatened to overflow

Adding Baking soda isn't going to help, if anything it will cause your HgCl2 to precipitate as elemental Hg, removing it from the rxn. The bubbles you saw were likely C02 being released

If you've got a failed amalgamation don't toss your solvent with oxime dissolved in it. Simply decant it, re amagamate and dump your solvent w/ oxime in again, (you might reduce the solvent volume so more of the sodium acetate falls out of solution, then filter it off) but your solution MUST be neutral or acidic or your HgCl2 will precipitate as I mentioned above.

Good luck

How do you explain basic reductive aminations like ketone/nitro or ketone/MeAm.HCl !?

The Al would have been fully amalgamated before the methylamine.HCl is neutralized with a base.  Pretty sure if you let the amalgumation proceed a little longer things will work for you.

I need to ask this again and I need answers ASAP!
Any advice is apreciated,I am very short on time but will give one of those reactions a try tommorow.

1.) Can I use dry IPA instead of dry EtOH to reduce oxime with Na!?
Does oxime need to be bone dry for this procedure?
Any advice on post reaction work-up and extraction?!

2.)What about this method. http://www.erowid.org/archive/rhodium/chemistry/oxime2amine.zn-af.html
I have both Zn and NH4Cl, ANY technical advice is more than apreciated.
For example,I don't want to filther mud like supstance (no celite!) so I assume I can
react amphoteric Zn with NaOH and extract with toluene just like normal Al/Hg procedure?!

1.) Can I use dry IPA instead of dry EtOH to reduce oxime with Na!?
Does oxime need to be bone dry for this procedure?
Any advice on post reaction work-up and extraction?!

i can't comment on the IPA, i've heard of it being used with other similar amalgamations with success so i'd assume Wizard X is giving good advice in his post.
no the oxime does not have to be bone dry, just as long as there isn't excess base present as an impurity (referring to excess base from the oximation).  i've used slightly wet oxime (sticky), and i've read madprossor's old posts on the hive where he's used wet oxime before as well with success.  but if you follow akcom's advice a few pages back or so, the final thing he does with the oxime is he washes it with HCl (he gives the molar amount, i can't remember off the top of my head but his post is in this thread somewhere).  washing it with HCl will allow the oxime to dry within hours instead of days

as far as the post reaction work-up just follow AB2's write-up word for word, although the reflux following the reaction doesn't seem to be necessary it certainly doesn't hurt, either way - whether you reflux after the reaction settles down a bit or not - you should let it stir for the amount of hours that AB2 says

Sucess!
Thanks guys!

I got some amine,it must be MDA or MDOH.

After I added all the sodium and left stirring on (reflux too) I left for a few hours
and when I came back...it solidified!
IPA probably could not escape and I got some weird smelling thing instead of it coming along the water.
I used procedure ala Sonson but used toluene instead of DCM (skipped washing it with non-polar while acid)
Stripped water under vacuum and transfered suspecting amine.HCl with IPA washes in evaporation dish.
(Hope IPA is good solvent for this)

It looks like a decen yield...

I didn't use Al/Hg at all. I used elementary Na in dry IPA ala Sonson.
WizardX helped me alot with his .pdf

is there any document on procedure?!

Have you done a literature search, or even typed the words "oxime reduction NaBH4" into google?

I hate to break it to you but that paper is discussing sodium cyanoborohydride reductions NOT sodium borohydride reductions you asked about in your previous post. You might want to hold off on trying to use either of those reagents until you are clear on the differences between the two.

Why don't you start a new thread, since you seem to have moved on to a new topic? This doesn't have anything to do with Antibodys acidic Al/Hg/HOAc reduction. I would just as soon Antibody's name not get brought to the top of the board every time you have question unrelated to anything she has done.

if you follow akcom's advice a few pages back or so, the final thing he does with the oxime is he washes it with HCl (he gives the molar amount, i can't remember off the top of my head but his post is in this thread somewhere).  washing it with HCl will allow the oxime to dry within hours instead of days

akcom, thanks bro much props to you, your 1M HCl wash works wonderfully!

the typical/most popular oximation procedure that people seem to use is to run the oximation, once the reaction is complete then you precipitate the oxime by putting the flask in an ice water bath and flooding the flask contents with ice cold distilled h2o.  the amount of ice cold h2o i add to the flask according to the oximation procedure i follow is 83% ratio to the alcohol v/v (i use EtOH) but you can feel free to use more if that's what you normally do.  adding all that ice cold h2o to the flask will form a homogenous solution with whatever alcohol you used (EtOH or MeOH), lowering the oxime's solubility and crashing it out.  you leave the flask in the ice water bath for a little while to make sure the flask contents are as cold as they should be and that you've precipitated all the oxime you could.  now either decant the alcoholic/h2o solution in the flask away from the oxime or vacuum filter the contents over filter paper leaving the oxime in the buchner funnel.  now begin the washes.  if you decanted then add the washes to the flask, swirl the liquid all around the oxime and then carefully decant the washes away from the oxime.  if you vacuum filtered then just wash the filter cake, let the wash solution sit in contact with the oxime for a little bit, use a stir rod to move the oxime around and try to get the wash solution to touch as much of the surface area of the oxime as possible, it will be gravity filtering during this time but that's ok, then you feel the oxime has been washed thoroughly then vac filter the oxime until dry for each wash.  the first wash is akcom's recommended 1M HCl wash, the volume of 1M HCl i use is equal to the amount of ice cold h2o i use to flood the flask and crash out the oxime.  the second wash is ice cold h2o, the volume of the ice cold wash is the same volume as the 1M HCl wash.  the third wash is ice cold h2o, the volume of the ice cold wash is the same volume as the 1M HCl wash.  the final two h2o washes are to remove residual acidic water to that the oxime is neutral.  antibody2's al/hg to reduce the oxime is acidic however it uses AcOH.  so i would assume it's important to remove any potential residual HCl from the oxime because i remember antibody2's old hive posts saying that he tried a number of acids for the acidic al/hg back when he was trying to find one that works and he said that when he used hcl it was too strong of an acid and the hcl itself actually sped up the amalgamation to a ridiculous pace.  so might as well play it safe and try to remove all the hcl from the 1M hcl wash from the oxime.

i vac filtered the oxime as dry as possible but the contents were still a little bit wet from the washes which can be expected of course.  i put the entire buchner funnel into a pyrex dish and let it air-dry a little bit, just dry enough so that i could scrape everything out of the buchner funnel without too much mess.  so then i scraped the oxime out of the buchner funnel and off the filter paper.  the oxime was nowhere nearly as sticky as it usually is, in fact i wouldn't even call it sticky.  it seemed a little clingy but that's it, by that i mean small amounts clung to the walls of the buchner and a little bit clung to the filter paper but not much.  i spread the oxime out as thin as possible and let it continue to air-dry.  by the end of the day, the oxime seemed bone dry.

one other observation is that on page 5, Oerlikon stated that the appearance of the oxime depends strongly upon the cooling/precipitation of the oxime.  i've found this to be true as well.  the oximation procedure i run is done at room temp and i just let it stir for a very long time (less heat = slower reaction), no heat or reflux required.  the heat/reflux is good for people who are pressed for time and need it done asap.  anyway once the oximation is complete and you're at the step where you're ready to flood the flask with cold water and clamp it into an ice bath to freeze precipitate - this seems to be the step that determines oxime appearance.  typically i run the oximation, then i flood the flask with ice cold water and clamp the flask into an ice water bath, so in other words it's a rapid precipitation.  doing it this way has always given me an oxime that looks like a white amorphous blob that is very sticky, so sticky that it clings to itself and that's how it become one big blob.  not too long ago i inadvertently attempted it a different way by accident.  since my oximation stirs for a long time (i let it stir for 16-24 hours due to a crazy work schedule).  so i ran the oxime and let it stir overnight, it just so happened to get really damn cold that night and when i checked back up on it again, to my surprise the oxime (or at least some of it) had precipitated already and i didn't even flood it yet.  it occurred to me that the slow drop in ambient temp that night while it was stirring caused the oxime to precipitate as the temp dropped.  the oxime was not a big white amorphous blob this time.  the slow cooling gave me oxime in the form of tiny white particulate.  they were somewhat sticky and clung together a little bit but not all that bad.  they were like little grains but they had no crystalline appearance whatsoever.  my oxime never has a crystalline appearance.  i then flooded the flask with cold h2o like i normally would and put it in an ice water bath, this may have precipitated a little more oxime i'm not sure, if it did precipitate more then it wasn't a noticeable amount.  so rapid cooling / fast precipitation seems to precipitate the amorphous oxime and slow cooling / slow precipitation precipitates the oxime as a tiny particulate.  the tiny particulate was by far easier to work with IMHO but both work just fine for antibody's al/hg reduction.