Does anybody know the mechanism of that reaction?
There are just formamide and formic acid as reactants. About 160 °C for 2-3 hours.
I´m looking forward to any suggestion.
It looks like a Leuckart type reaction (reductive amination with formamide at high temp) followed by acid catalysed elimination
I think the reduction to the hydroxide is not possible using formic acid (cyclic transition state via Leuckart). Otherwise I wonder how elimination of a primary amine should work under these conditions. Also a strong acid is missing for step 2 of the Leuckart reaction.
Formic acid is a polar solvent & stronger acid. As you are heating at a higher temperature 160 deg. hydrolysis is possible catalyzed by acid with the formation of the formic acid & ammonia.
Interessting Question :)
Accordng to this https://en.wikipedia.org/wiki/Leuckart_reaction The reaction of a ketone with formamide is possible. As an intermediate one would obtain the formylamine.
What if this "amide-group" is the leaving group? Acid catalysis could be possible...Amide gets protonated, alpha-Proton (in respect to nitrile) dissociates, double bond is formed, formamide is formed as by-product.
Dissociation of the alpha-Proton seems to be the missing link. I think I just get it.
Thank's a lot to all of you and your support.
Its just an idea...not sure if thats the true mechanism. But really interessting reaction.
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