foxy2 (Hive Bee)
08-24-00 19:26
No 44915
      Amide Reduction Alternatives  Bookmark   

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???

Foxy out
08-24-00 23:06
No 44974
      Re: Amide Reduction Alternatives  Bookmark   

I wish that sodium borohydride would work but I don't think so. I wonder what lithium in ammonia would do.
08-25-00 04:47
No 45083
      Re: Amide Reduction Alternatives  Bookmark   

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... smile
(Sexy, Sexy, Sexy)
08-28-00 05:03
No 46282
      Re: Amide Reduction Alternatives  Bookmark   

Red-Al will reduce the amide too.
(Hive Bee)
08-28-00 06:22
No 46291
      Re: Amide Reduction Alternatives  Bookmark   

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