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Topic: Red-Al reduction of nitrile to amine?  (Read 440 times)

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Offline Reddart

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Red-Al reduction of nitrile to amine?
« on: March 06, 2019, 03:41:57 PM »
Wiki says "yes"

Organic-chemistry.org says "No" (goes to aldehyde).

What say you?

Offline phth

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Re: Red-Al reduction of nitrile to amine?
« Reply #1 on: March 07, 2019, 01:46:15 AM »
Under what conditions? I have seen some examples of alkoxy aluminum dihydrides reducing things to aldehydes, but typically those procedures use low temps e.g. -78º taking advantage of the increased solubility. I think that more forcing conditions should work besides the reactivity of the hydrides being lowered due to the alkoxy ligands.

Offline Reddart

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Re: Red-Al reduction of nitrile to amine?
« Reply #2 on: March 07, 2019, 02:31:34 PM »
OK, that sounds good. I'll find out soon enough when my Red-Al comes in.

Offline wildfyr

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Re: Red-Al reduction of nitrile to amine?
« Reply #3 on: March 07, 2019, 04:05:37 PM »
Aldehydes are a delicate beast when it comes to reductions, my money would be on the ability to reduce it all the way if you kick it in the pants a bit with heat/equivalencies.

Offline rolnor

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Re: Red-Al reduction of nitrile to amine?
« Reply #4 on: March 09, 2019, 09:00:55 AM »
If you want aldehyde I think DIBAL/-78°C is a good reagent, with NaBH4/NiCl/MeOH you get the amine.

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