cheap& easy methylamine from methyl nitrite reduction-La

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dormouse
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04-20-00 22:46
No 108469




Cheap & easy methylamine from methyl nitrite reduction!-Labrat
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Cheap & easy methylamine from methyl nitrite reduction!

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Author Topic:   Cheap & easy methylamine from methyl nitrite reduction!
Labrat
Member   posted 08-12-98 10:50 AM
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Probably most of you know that methylamine can be synthesized by reduction of nitromethane. Although this is an attractive route, nitromethane is still pretty expensive in Labrat's opinion. There has to be a better way!
And there is! And this route is reduction of methyl nitrite. A lot of people have already
worked with methylnitrite already, so this should pose no problem. Since this substance is a gas at room temp I propose this scheme:

1)The methylnitrite is generated by dripping H2SO4 into a solution of NaNO2 in MeOH.

2)The gas is bubbled through an alcoholic suspension of aluminum amalgam. The gas is reduced to methylamine, which is also a gas at room temp.

3)The gases evolving from the amalgam suspension are bubbled through an alcoholic solution of HCl. The methylamine will form the salt with HCl, methylnitrite won't react and will vent off. Evaporate the alcohol to get your methylamine.HCl in very pure form!

Now, I think you'll agree this is a very good method! It's done before. For example, check out Ann. Chim. Phys. 25:136('64). In this case the hydrogenated the nitrite to get the amine, but aluminum amalgam will do the job. Have fun cooking! Lr/

ChemHack
Member   posted 08-12-98 11:22 AM
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"2)The gas is bubbled through an alcoholic suspension of aluminum amalgam. The gas is reduced to methylamine, which is also a gas at room temp. "
Labrat,
Let me show my IG-nor-Ance and ask:
What keeps the methylamine gas from just staying in the alcohol?

quirks
Member   posted 08-12-98 04:27 PM
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methyl/ethyl nitrite can be used as the amine source directly in the amalgamation instead of methylamine, no need to do that.

Labrat
Member   posted 08-13-98 10:27 AM
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ChemHack: the only thing you're showing is that you can't read very well. You did seem to manage to read step 2, where I mention that the methylnitrite is reduced by aluminum amalgam to methylamine gas. But then you fail to read step 3, where I mention that the gases evolving from the amalgam solution should be bubbled thru alcoholic HCl! That way you'll get an alcoholic solution of methylamine.HCl. It's easy to recover the methylamine.HCl by evaporating the alcohol + excess acid.
quirks: you probably mean that nitromethane can be used directly to produce methylamine in situ by amalgam reduction, right? I've never seen anybody mentioning that methyl/ethyl nitrite can be used as substitutes for nitromethane to produce methylamine in situ. Lr/

quirks
Member   posted 08-13-98 11:46 AM
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I thought I seen nitrite somewhere...
Isn't nitrite CH3-O-N=O? How does Al reduce that?

drone 342
Member   posted 08-13-98 12:41 PM
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Well, I'm gonna have to call you on this one, labrat. Do you have ref's for nitrite reduction via aluminum amalgam? I assume you mean:
1) methyl nitrite is reduced to methylamine

2) methylamine reacts accordingly.

But are you sure that aluminum will do the trick here? Why?

I must say, if this works half as slick as it sounds, this is a great contribution, and I thank you for it. Still, by nature I'm a skeptic, and it never hurts to ask.

-drone --342

ChemHack
Member   posted 08-13-98 02:25 PM
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Labrat,
I really was asking a stupid question, I can read just fine!!! The stupid question is to what extent is methyalmine gas soluabe in the alcoholic solution. Sure MeAm.HCl is soluable, but is plain methylamine gas and, if so, wouldn't you end up with a saturated solution of it before any went over into to acidified alcohol?

drone 342
Member   posted 08-13-98 03:03 PM
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I found an example of a nitrostyrene being reduced by aluminum amalgam. I haven't gotten a copy of the actual ref yet, buy alledgedly it was used to reduce 2,3-dimethoxy-b-nitrostyrene into 2,3-DMPEA.
Reaction 1 of 3
Reaction ID 320290
Reactant BRN 2096801 2,3-dimethoxy-phenethylamine
2645541 <2,3-dimethoxy-phenyl>-acetic acid
Product BRN 3466970 <2,3-dimethoxy-phenyl>-acetic acid-<2,3-dimethoxy-phenethylamide>
Reaction Classification Preparation
Temperature 160 ¯C
-------------------------

Reaction 2 of 3

Reaction ID 363409
Reactant BRN 2506022 1,2-dimethoxy-3-(2-nitro-vinyl)-benzene
Product BRN 2096801 2,3-dimethoxy-phenethylamine
Reaction Classification Preparation
Reagent amalgamated aluminium
aq.-ethanolic acetic acid
-------------------------

Reaction 3 of 3

Reaction ID 468392
Reactant BRN 3273510 <2,3-dimethoxy-phenyl>-acetaldehyde-oxime
Product BRN 2096801 2,3-dimethoxy-phenethylamine
Reaction Classification Preparation
Reagent sodium-amalgam
ethanolic acetic acid

drone 342
Member   posted 08-13-98 03:37 PM
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here's one detailing the use of nitromethane as the reagent involved in aluminum amalgamation reductive amination of phenylacetones:
Reaction

Reaction ID 175261
Reactant BRN 1698205 nitromethane
2502308 <2-methoxy-phenyl>-acetone
Product BRN 2803353 (+-)-<2-(2-methoxy-phenyl)-1-methyl-ethyl>-methyl-amine
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Reaction Details

Reaction Classification Preparation
Reagent amalgamated aluminium
ethanol
Ref. 1 2262789; Journal; Tanaka; Seki; YKKZAJ; Yakugaku Zasshi; 77; 1957; 310; Chem.Abstr.; 1957; 11278;

-drone --342

David
unregistered   posted 08-13-98 08:38 PM
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ChemHack:
Chill out there dude, I see what you're asking. Maybe heating it a little would work...

Rhodium
Administrator   posted 08-14-98 04:23 AM
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Excuse me, Drone --342, but you left out the actual ref in your post about Al/Hg reduction of nitroalkenes...

quirks
Member   posted 08-14-98 10:20 AM
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I have the chem abstracts on it, and that is the journal name "yakugaku zasshi", --77, pg 310-11 (1957)
Anybody want to go to the effort of getting that interlibrary loan?

Anyways, it says

"2-MeCH:CHC6H4OMe (52g) in 400ml AcOH treated portionwise with 200g. Pb3O4 stirred 1 hour at 40 degrees, the solution treated with a small amount of H2O, AcOH removed in vacuo, the residue extracted with Et2O, the Et2O residue with 500ml 20% H2SO4 refluxed 3 hrs, and the end product with EtO2 gave 24g 2-MeOC6H4CH2COMe (I), I (32.8g) in 19g MeNO2 and 100ml EtOH added dropwise to 30g Al-Hg in 500ml EtOH, refluxed 2-3 hours, the Al(OH)3 and EtOH removed, the residue acidified with HCl, washed with Et2O, made alkaline with NaOH, and the end product extracted with Et2O gave 29g 2-MeOC6H4CH2CH(NHMe)Me."

Labrat
Member   posted 08-14-98 10:37 AM
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ChemHack: David already gave the answer: heating the alcoholic solution will do the trick, otherwise adding some solid NaOH or KOH will certainly do the trick!
Drone: good to have some critics on this! Then I can explain why I think it could work. I haven't got a ref where methyl nitrite is reduced by Al/Hg to methylamine. But have you already checked the article I gave? (Ann.Chim.Phys 25:136('64)

In this article the author does mention that several reducing agents failed to do the reduction: SnCl2, Fe/HCl, Zn/acetic acid. But the author mentions that the reductions failed because there were done under hydrous conditions! That's why I mention using alcoholic aluminum amalgam to reduce the nitrite. BTW, no mention of an attempt to reduce the nitrite with Al/Hg in the article.

The author proposes a lot of mechanisms for the reaction. Only one corresponds to the observations made: the methyl nitrite first isomerises to nitromethane, then the nitromethane is reduced by Al/Hg, which is a known reaction. The only problem I see here is that Al/Hg is not capable of isomerising methyl nitrite to nitromethane, but since nobody tried I thought let's give it a try!

The article I mentioned is about hydrogenating alkyl nitrite, c.q. methyl nitrite with Ni or "cuivre" (?). The reaction temp is usually >250 C. When operating under these high temperatures, most nitrite is reduced to dialkylamines and alkylamines.

OK, that's all the facts I have. If you're sceptical about it, don't worry, I'm still a little sceptical about this reaction too. But since the chemicals needed are so trivial it would be a fucking shame if nobody tried it.
The method I proposed makes it easy to see if any amine is formed, the only thing we need now is somebody to test it. I'm very curious if this drag-queen fuel could substitute for drag-star fuel to make methylamine... Lr/

Labrat
Member   posted 08-14-98 10:49 AM
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Drone: thanks for checking the Beilstein! Actually I was interested in nitromethane/ketone reduction by Al/Hg to the amines we all know and love. You're giving me more then I asked for, what else could a guy want?
The ref you found (Yakugaku Zasshi) was already mentioned in "Amphetamine Synthesis..." by Otto Snow. It seems that Snow did a pretty good job cruising the search engines, since this seems to be the only case wherein nitromethane was reduced in situ to methylamine and ultimately forming the amphetamine in a practical one-pot procedure. Too bad it's in Japanese, since nobody out here can read that freaky language. Is there a Japanese bee out here?

You found some refs on nitrostyrene reduction with Al/Hg too. The only thing I found in the literature was that this reduction usually doesn't proceed any further then the oxime and the yield is REALLY lousy! This seems like a dead-end to me. But if you'd be so kind to provide us with some refs, we could check them too. Later man. Lr/

drone 342
Member   posted 08-14-98 02:48 PM
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Damb! I see what you guys mean! I'll get back to you on that, but the ref I was talking about was:
Yakugaku Zasshi; 77; 1957; 310; Chem.Abstr.; 1957; 11278. I'll be nice and type in a copy for everybody (if it ain't in Japanese.)
I'll keep looking for that nitrostyrene reduction, but I know its out there. Actually, the way that looks most appealing is a electrolytic reduction -- yields are fair ( 60-70%), reagents are common (H2SO4, iPrOH, H2O), and conditions are reasonable. I have all the literature on it at home. Its out there.

-drone --342

drone 342
Member   posted 08-14-98 03:07 PM
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Here's a list of a few different examples of reductive aminations of ketones using nitroalkanes. There's only one that's explicitly PEA chemistry, but the remainder are interesting enough in their own right. Examining the conitions of these related reactions provides greater understanding of our own field of chemistry. Here you go:
Reactant BRN 1698205 nitromethane
2502308 <2-methoxy-phenyl>-acetone
Product BRN 2803353 (+-)-<2-(2-methoxy-phenyl)-1-methyl-ethyl>-methyl-amine
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Reaction Details

Reaction Classification Preparation
Reagent amalgamated aluminium
ethanol
Ref. 1 2262789; Journal; Tanaka; Seki; YKKZAJ; Yakugaku Zasshi; 77; 1957; 310; Chem.Abstr.; 1957; 11278;

Reaction

Reaction ID 744551
Reactant BRN 635680 propan-2-one
3522252 tetrakis-<3-nitro-phenyl>-silane
Product BRN 3516547 tetrakis-<3-isopropylamino-phenyl>-silane
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Reaction Details

Reaction Classification Preparation
Reagent tin
aqueous hydrochloric acid
Ref. 1 2295542; Journal; Kipping; Blackburn; JCSOA9; J.Chem.Soc.; 1935; 1085,1086;

Reaction

Reaction ID 1073224
Reactant BRN 2044332 <4-methoxy-phenyl>-acetone
6319980 C17H18N2O4*ClH
Product BRN 2405810 C27H30N2O5
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Reaction Details

Reaction Classification Preparation
Reagent NaBH3CN
Solvent methanol
Ref. 1 400608; Patent; Takeda; FR 2274287; 1975; FR; DE 2525512; 1975; Chem.Abstr.; EN; 85; 20934; 1976;

Reaction

Reaction ID 2016180
Reactant BRN 1907123 4-phenyl-butan-2-one
5552038 C12H16N2O3
Product BRN 5770029 C22H28N2O3
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Reaction Details

Reaction Classification Preparation
Reagent NaBH3CN, HCl (20percent)
Solvent methanol
ethanol
Other conditions Ambient temperature
Note 1 Yield given
Ref. 1 5679385; Journal; Itoh, Katsumi; Miyake, Akio; Tada, Norio; Hirata, Minoru; Oka, Yoshikazu; CPBTAL; Chem.Pharm.Bull.; EN; 32; 1; 1984; 130-151;

Reaction

Reaction ID 2016194
Reactant BRN 1907123 4-phenyl-butan-2-one
5670697 C11H14N2O4*ClH
Product BRN 5689074 C21H26N2O4*ClH
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Reaction Details

Reaction Classification Preparation
Reagent 1.) NaBH3CN; 2.) HCl/EtOH
Solvent methanol
Yield 68. (BRN5689074)
Temperature 5 ¯C
Ref. 1 5668132; Journal; Miyake, Akio; Itoh, Katsumi; Tada, Norio; Tanabe, Masao; Hirata, Minoru; Oka, Yoshikazu; CPBTAL; Chem.Pharm.Bull.; EN; 31; 7; 1983; 2329-2348;

Reaction

Reaction ID 2104235
Reactant BRN 2208358 4-nitro-phenethylamine
6515172 C18H16O2
Product BRN 6577899 C26H26N2O3
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Reaction Details

Reaction Classification Preparation
Reagent NaBH3CN
Solvent methanol
Time 72 hour(s)
Ref. 1 5837722; Journal; Carson, J. R.; Almond, H. R.; Brannan, M. D.; Carmosin, R. J.; Flaim, S. F.; et al.; JMCMAR; J.Med.Chem.; EN; 31; 3; 1988; 630-636;

Reactant BRN 508690 4-nitro-aniline
635680 propan-2-one
Product BRN 2092075 N-isopropyl-4-nitro-aniline
-------------------------

Reaction Details 1 of 3

Reaction Classification Preparation
Reagent NaBH4, 3 M H2SO4
Solvent tetrahydrofuran
Yield 90. (BRN2092075)
Other conditions 1.) 0 deg C, 2.) room temperature, 40 min
Ref. 1 5718972; Journal; Verardo, Giancarlo; Giumanini, Angelo G.; Strazzolini, Paolo; Poiana, Marco; SYNTBF; Synthesis; EN; 1; 1993; 121-125;
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Reaction Details 2 of 3

Reaction Classification Preparation
Reagent 1.) HCl, 2.) sodium cyanoborohydride
Other conditions 1) methanol; 2) overnight
Note 1 Yield given. Multistep reaction
Ref. 1 5625957; Journal; Parr, William J. E.; JCPRB4; J.Chem.Soc.Perkin Trans.1; EN; 1981; 3002-3007;
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Reaction Details 3 of 3

Reaction Classification Preparation
Reagent 1.) 12N HCl, 2.) NaBH3CN
Other conditions 1.) MeOH, RT, 1 h, 2.) MeOH, RT, 2 h
Note 1 Yield given. Multistep reaction
Ref. 1 6049273; Journal; Kuyper, Lee F.; Baccanari, David P.; Jones, Michael L.; Hunter, Robert N.; Tansik, Robert L.; et al.; JMCMAR; J.Med.Chem.; EN; 39; 4; 1996; 892-903;

Reaction

Reaction ID 3527880
Reactant BRN 635680 propan-2-one
6818396 C14H20N4O4
Product BRN 6819588 C17H28N4O2
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Reaction Details

Reaction Classification Preparation
Reagent 1.) acetic acid, 2.) NaCNBH3
Other conditions 1.) methanol, 0 deg C, 15 min, 2.) methanol, 0 deg C - RT
Note 1 Yield given. Multistep reaction
Ref. 1 5899013; Journal; Romero, ***** L.; Morge, Raymond A.; Biles, Carolyn; Berrios-Pena, Norman; May, Paul D.; et al.; JMCMAR; J.Med.Chem.; EN; 37; 7; 1994; 999-1014;

Reaction

Reaction ID 4629554
Reactant BRN 508690 4-nitro-aniline
741880 butan-2-one
Product BRN 2719799 N-sec-butyl-4-nitro-aniline
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Reaction Details

Reaction Classification Preparation
Reagent 1.) 12N HCl, 2.) NaBH3CN
Other conditions 1.) MeOH, RT, 1 h, 2.) MeOH, RT, 2 h
Note 1 Yield given. Multistep reaction
Ref. 1 6049273; Journal; Kuyper, Lee F.; Baccanari, David P.; Jones, Michael L.; Hunter, Robert N.; Tansik, Robert L.; et al.; JMCMAR; J.Med.Chem.; EN; 39; 4; 1996; 892-903;

drone 342
Member   posted 08-14-98 03:11 PM
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Here's the nitrostyrene reduction material. Like I said, I haven't looked them up yet, so I can't guaruntee their quality:
Reaction Details 1 of 5

Reaction Classification Preparation
Reagent amalgamated zinc
aqueous hydrochloric acid
Ref. 1 2252430; Journal; Tsatsas; APFRAD; Ann.Pharm.Fr.; 7; 1949; 733, 741;
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Reaction Details 2 of 5

Reaction Classification Preparation
Reagent amalgamated aluminium
aq.-ethanolic acetic acid
Ref. 1 2252427; Journal; Spaeth; Riedl; Kubiczek; MOCMB7; Monatsh.Chem.; 79; 1948; 72, 77;

-drone --342

6079 Smith W
unregistered   posted 08-14-98 07:05 PM
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If that yakugaku zasshi ("pharmaceutics journal") item is written in romaji instead of kanji/hiragana/katakana characters (I doubt this), I can *probably* translate it. If not, I know someone else who could do it... although I don't know how you'd post it short of an image scan (on the assumption that if you had & could use markup software, you could translate it yourself).

Labrat
Member   posted 08-17-98 09:51 AM
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Drone: you're very right about electrolytic reduction being a good alternative for hydride reductions of nitroalkenes. I recall a very good article of Slotta and Heller in the J.Prak.Chem., where the authors have investigated what gives the best yield of amine from nitroalkene. If you want I can give you the exact ref, but it's somewhere out here in the posts already. The yields were excellent, usually >80%.
About the Yakugaku Zasshi article, it would be great if somebody could get this thing, even if it's in Japanese. It's possible to send that article to a professional translator for a small fee. Maybe we can hire one especially for the Hive, cuz there are more interesting Japanese article around. Lr/

drone 342
Member   posted 08-17-98 01:51 PM
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I'm sitting here with a copy of the Yakugaku Zasshi article in front of me, and just as I feared, it's in Japanese. Though I have absolutely no understanding of the written (or spoken) Japanese language, I can see that the experimental sections in both versions appear essentially the same -- this I was able to deduce from the scant chemical names that appear and the numbers.
Though the ketone synth that they provide looks like a real low-yielding method, its ease makes it a nice otc route (as everybody knows, lead tetroxide is used in glazes for ceramics, as well as a lot of other artsy-craftsy things. Its the stuff you were told as a kid not to eat.) Then again, maybe this isn't such a bright idea.

Regardless, the subsequent amine synthesis is certainly worthwhile, and when I get access to a scanner, I'll send y'all a copy of the original article. I'll let someone else worry about translation.

Anyways, there's at least one part (aside from the abstract) of this article written in English -- the bibliography:

JACS 60, 465, (1938)
JACS 62, 922, (1940)
JACS 75, 921, (1953)
Org. Reactions 2, 26 (1944)

Stonium
Member   posted 08-17-98 07:56 PM
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Labrat: Check out http://www.neocor.com/. I just took a quick glance at this website so I could be mistaken, but this seems to be Japanese translation software with a 15 day free trial download. Hope this helps.
Stonium

Osmium
Member   posted 08-18-98 05:36 AM
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I tried this reaction in my Al/Hg experiments. This reduction of MeNO2 is very exothermic, and doing it with foil is probably no good idea. Yields are lower with this variation compared to aq. MeNH2, because it's difficult to extract all that Al sludge. When you try to use more MeNO2 to produce more MeNH2 in situ, things get worse, because much more Al is needed to reduce the MeNO2 compared to the imine, meaning even more sludge to extract.
imine + 2[H] ----> amine
MeNO2 + 6[H] ----> MeNH2 + 2 H2O

Al + 3 H2O ------> Al(OH)3 + 3[H]

This means that in theory 2 moles of Al are needed to reduce one mole of MeNO2, plus another 0.667 moles Al to reduce the imine. Usually 2x excess Al is used in Al/Hg, because much of it will be lost due to side reactions (Shulgin uses even more). Aiming for a decent excess of MeNH2 is therefore quite difficult.

Osmium
Member   posted 08-18-98 05:40 AM
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And I seriously doubt that MeONO can be reduced to MeNH2. If this really works, I will personally suggest you for the Nobel Price this year Wink

Labrat
Member   posted 08-18-98 10:25 AM
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Drone: your library is alot better then mine!
But like I told ya, that article is in Japanese. Accidently I have a friend who studies Japanese, but I don't think he can read chemical language. I'll see what I can do and I'll keep you posted on the results.
Stony: I've checked that site out, but you'll have to fill in an ENORMOUS form to get the free download copy of the Japanese-English translator program! Drone said he'd be so nice to send all of us a copy, so as soon as I have that article, I'll fill in that lengthy form and see what that program can do. Thanks for the tip!

Os: I'm not sure either if methylnitrite can be reduced to methylamine, but unless you try, you'll never find out. This is what chemistry is about, trying new things. If I had all the necessary chems, I would have tried it before posting, but I've moved recently and all my stuff is still not in place. Lr/

drone 342
Member   posted 08-19-98 06:34 PM
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Here is a copy of the original Japanese article "Yakugaku Zasshi". I checked the Statsbot for lycaeum, and I know that its visited by some folks from Japan; please, kind Japanese folks, if you can, translate this for the rest of us silly English-speaking monkeys. Geez, somebody out there must be able to speak this language! http://www.geocities.com/CapeCanaveral/Hall/1399/yakugakuzasshi1.jpg
http://www.geocities.com/CapeCanaveral/Hall/1399/yakugakuzasshi2.jpg

Part 1 (approx 450 k)

Part 2 (approx 200 k)

I didn't add the images to this message since the first part is around 420 kb, and the second part is around 200, and I figured that would just piss off a lot of people with slow machines. Still, for your parousal, its there. Enjoy.

-drone --342

6079 Smith W
unregistered   posted 08-19-98 08:51 PM
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I'll do as much as I can, but someone else is more than welcome to beat me to it...

Labrat
Member   posted 08-20-98 09:51 AM
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Drone: you're a man who keeps his word! Thanks! I'll see whether I can find anybody/anything to translate that article.
Smith: I'll try to beat you to it! Lr/

6079 Smith W
unregistered   posted 08-27-98 07:05 PM
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Just a quick update... I passed this so far through two fluent speakers with decent literacy, and one native Nihon-jin (one of the other guys' mom). The first two kind of went "huh?" and the mom either couldn't or wouldn't translate a technical document (the wording was ambiguous). So now I am waiting to hear if the father (another native, who happens to be an engineer) can/will help. Meanwhile, I am trying to find a couple old acquaintences...
Like I said, anyone else is still welcome to beat me to the punch!

BTW, there are some nice programs here available for demo, including an OCR that I didn't have much success with...

Labrat
Member   posted 08-28-98 10:41 AM
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I've also had little succes in getting a decent translation. The translation program Stonium found only produced twisted language that was no good.
I tried to get the thing translated at the Academy of Japanese Literature, but when I got there yesterday, there was nobody who could translate this kind of technical language.

Now I'm waiting till somebody at the University Library comes back. That certain somebody could read technical Japanese, I was told. So all my hopes are now focused on this guy. Lr/

Piglet
Member   posted 09-04-98 05:59 AM
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Some while ago a discussion about the production of nitroalkanes suggested that a halide could be swapped with silver nitrate which supposidly worked %40 but was a little expensive. It was stated that other nitrates yielded nitrites.
Question:

Can NaNO2 be reacted with halosafrole and then reduced to the amine? This would bee nice, wouldn't it!

pambaruka
Junior Member   posted 10-02-98 08:42 PM
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so how do isomerize the nitrite again???