Author Topic: Amide Reduction Alternatives  (Read 1163 times)

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foxy2

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Amide Reduction Alternatives
« on: August 24, 2000, 07:26:00 PM »
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

  • Guest
Re: Amide Reduction Alternatives
« Reply #1 on: August 24, 2000, 11:06:00 PM »
I wish that sodium borohydride would work but I don't think so. I wonder what lithium in ammonia would do.

Lilienthal

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Re: Amide Reduction Alternatives
« Reply #2 on: August 25, 2000, 04:47:00 AM »
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

  • Guest
Re: Amide Reduction Alternatives
« Reply #3 on: August 28, 2000, 05:03:00 AM »
Red-Al will reduce the amide too.


http://rhodium.lycaeum.org


foxy2

  • Guest
Re: Amide Reduction Alternatives
« Reply #4 on: August 28, 2000, 06:22:00 AM »
Thanks Rhod
Too bad an order for some Vitride would look pretty suspicious.
Oh well