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foxy2
(Hive Bee) 08-24-00 19:26 No 44915 |
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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??? Thanks Foxy out |
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terbium (Stranger) 08-24-00 23:06 No 44974 |
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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. |
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Lilienthal (Moderator) 08-25-00 04:47 No 45083 |
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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... ![]() |
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Rhodium (Sexy, Sexy, Sexy) 08-28-00 05:03 No 46282 |
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Re: Amide Reduction Alternatives | Bookmark | |||||
Red-Al will reduce the amide too. http://rhodium.lycaeum.org |
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foxy2 (Hive Bee) 08-28-00 06:22 No 46291 |
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Re: Amide Reduction Alternatives | Bookmark | |||||
Thanks Rhod Too bad an order for some Vitride would look pretty suspicious. Oh well |
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