[groggybeer]

I need help regarding the mechanism of the reduction taking place in this reaction: http://www.orgsyn.org/Content/pdfs/procedures/CV2P0526.pdf
I searched the web and tried to find a mechanism myself but i was not successful so far.
It is clear, that the amide is deprotonated by the NaOH and the resulting negative charge is stabilized by delocalisation. But how is the carbon reduced? It seems unlikely to me that the zinc just donates its electrons to the carbon with fairly high electron density.
If anyone could be so kind and help me find the mechanism i would appreciate it very much!

[rolnor]

There is some typical dissolving-metal reductions like Birch, here is one example with zinc; https://www.organic-chemistry.org/namedreactions/clemmensen-reduction.shtm

I am not sure of the exact mechanism in you reduction, I think it is complicated.

[groggybeer]

yes, i have looked at the clemmensen reduction, however in the phthalimide reduction results in an alcohol and an acid and not in an alkane.. Plus every metal reduction is in acidic conditions. The Phthalimid reduction is in basic conditions. This too doesn't make sense to me.

[AWK]

Phthalic acid, phthalic anhydride, and phthalimide can be reduced to phthalide with zinc, tin, and aluminum in both alkaline and acid conditions. The reaction has been known for about 100 years and nobody cared about its mechanism then. In addition, many reduction reactions and oxidation reactions with oxygen do not yet have a fully elucidated reaction mechanism. You may be the first.

[wildfyr]

"The reaction has been known for about 100 years and nobody cared about its mechanism then"

lol

[groggybeer]

Ok thank you for the information.