Amide Reduction Alternatives

[foxy2]

Hypothetically say one reacted 3-INDOLEACETIC ACID with dimethylamine to get the amide.  Are there any ways of reduceing this amide without LAH, NaBH4 or other special reduceing agents that must be purchased via a chem supplier???

Thanks
Foxy out

[terbium]

I wish that sodium borohydride would work but I don't think so. I wonder what lithium in ammonia would do.

[Lilienthal]

Foxy: 3-indoleacetic acid will not react with dialkylamines without further activation (e.g. with carbodiimides or as an acid chloride or anhydride).

Pure NaBH₄ wouldn't work for reduction of amides. NaBH₄ + activator (e.g. Lewis acids) will reduce amides, but will probably also reduce the indole to indoline (2,3-dihydroindole), at least to some extent. The same is true for borane BH₃.

Terbium: Lithium (as well as sodium) in liquid ammonia is a strong base and will only reversibly deprotonate the indole (and maybe the alpha-CH₂).

So LiAlH₄ is the reagent of choice for amide reduction in this case. I'm not aware of other (practical) routes. Maybe there are some obscure bath tub methods...  

[Rhodium]

Red-Al will reduce the amide too.

http://rhodium.lycaeum.org

[foxy2]

Thanks Rhod
Too bad an order for some Vitride would look pretty suspicious.
Oh well