CH3NO2 --->CH3NH2 reaction mechanism

[zero_nrg]

Can anyone provide details of the reaction mechanism to convert nitromethane to methylamine (TFSE N/A).  Seem to recall a post where some bee asked why the Al/Hg reduction of nitromethane wasn´t done in such a way that there was not enough solvent around for the gas to dissolve in and it would then be piped out of the reaction and dissolved directly into cold MeOH (after drying it etc).  Does the reaction requires a protonic solvent to proceed.  -zero

[ning]

Use Rhodium's Fucking Search Engine

https://www.thevespiary.org/rhodium/Rhodium/chemistry/methylamine.pdc.html

https://www.thevespiary.org/rhodium/Rhodium/chemistry/eleusis/methylamine27.html

https://www.thevespiary.org/rhodium/Rhodium/chemistry/methylamine.html

Rhodium has a lovely personal site.
And don't forget google

Now, to address more technical parts of your questions:

1. Yes, the solvent should be protic. Where else can the hydrogens come from? The dissolving metal is the battery, it forces them to move. But they still need to come from somewhere.

2. If they are using BASIC conditions, I imagine the reaction would produce methylamine gas. You could run the reaction really cold to keep it from evaporating, but why not just use an acidic dissolving-metal reduction instead? Then it would produce MeNH2.HCl, which I can guarantee you won't go turning into a gas so easily.

More to the point, why bother making methylamine from nitromethane at all, when there's much more efficient methods available? Do a hoffmann rearrangement on acetamide and save that aluminum and mercury for the reductive amination! And keep your nitromethane for when some useful aldehydes cross your path!

If you're really so interested in mechanism, I'm sure one of the more knowledgeable staff members would be happy to share their knowledge. All I know is that it's got many steps.