Glass mycologist
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Nitromethane synthesis from methylamine
Hi there
I tried to look online for the nitromethane synthesis from methylamine but it's not very popular.
I found that oxidation of primary amine to nitro compounds is done using ozone or peroxides but does anyone have a procedure involving more "common"
reagent ?
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BluBoirt
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This could give you some starting point. But maybe using chloroacetic acid as a starting material would be better than MeNH2.
https://patents.google.com/patent/CN102190587A/en
[Edited on 3-11-2020 by BluBoirt]
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Herr Haber
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I looked that up a couple of months ago when people were talking about ozone as a disinfectant.
Oddly enough I discovered some research paper where they would further react the produced nitromethane with chlorine with obvious results.
The spirit of adventure was upon me. Having nitric acid and copper, I had only to learn what the words 'act upon' meant. - Ira Remsen
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Opylation
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I was looking at a bunch of different resources a little bit ago for the preparation of nitroalkanes. This one looks like the best process that has
detailed instructions http://www.orgsyn.org/demo.aspx?prep=CV1P0401
I was also looking at oxidation of amines as a route. Now the oxidation of plain amines is a little tedious as you have to work up to nitro through a
few different oxidation states and it didn’t seem too straight forward. One process though that looks really intriguing is oxidation of alpha-amino
acids and then subsequent decarboxylation. Alpha-nitro acids easily decarboxylate via a similar mechanism to beta-oxoacids. I also thing the carbonyl
aids in oxidation or at least promotes it. Look into oxidation of glycine. Decarboxylating the nitroacid will be a breeze
[Edited on 9-11-2020 by Opylation]
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njl
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@Opylation I have also done some reading about amine --> nitro and I think going from amine to oxime and then oxidizing to nitro is a good method.
I don't have a procedure or anything but if I recall correctly the oxidation of primary amines to oximes is fairly gentle.
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