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Reducing amides to amines

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Chimimanie:
Great find Lego!  8)

Someone has to try it on a more interesting substrate!  ;D

1,4-dimethoxybenzene is a good choice.  ;)

Herr_Ovalmeister:
See
Post 311068 (PolytheneSam: "Electrochemical reduction", Tryptamine Chemistry)

Zamboni:
In column 4 lines 17+ of
Patent US5074974
it says


an oxidation synthesis can be conducted in an electrochemical cell divided by an anion-exchange membrane. In this instance, the anolyte will be the working electrolyte, and anions will selectively flow through the membrane from the catholyte (counter electrolyte) into the anolyte. Or, alternatively, a reduction synthesis can be conducted in a cation-exchange membrane-divided cell. In this example, the catholyte will be the working electrolyte, and cations will be be selectively exchanged from the anolyte (counter electrolyte) through the membrane to the catholyte (working electrolyte).

--- End quote ---



US 5074974 has the same inventor listed as the patent here:
Post 312706 (PolytheneSam: "US 4,695,352", Tryptamine Chemistry)

Zamboni:
Note the use of titanium here:
Patent US742797
Patent US4695352

java:
I have been looking for a specific method to remove the amide formed on Phenylalalnie via acylation that is being used as a protecting group while the COOH is being reduced to CH3. I've considered the -OBr method but it's limited to aliphatics and the catalytic reduction seems not doable with my Parr Hydrogenator that is limited to 60 p.s.i.. in reducing the amides without making the amide a better leaving group. By doing it this way it leave a methyl amine hence the finish product is a meth-amphetamine as opposed to just amphetamine

I've read the methods suggested by Lego and others in converting the amide to easier leaving groups, thioamides, that can be removed easily but need ....

The Preparation and Chemical Properties of Thionamides.
Richard N. Hurd, George DeLaMater;
Chem. Rev.61(1); 45-86,1961

this method might work and  the removal by catalytic hydrogenation appeals to me....java

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