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Author Topic: Raney Ni reduction of nitrile  (Read 2277 times)

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starfish

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Raney Ni reduction of nitrile
« on: November 08, 2011, 06:19:58 PM »

Hello,

I am new to this forum. Just to say hi to all of you first.
I got trouble with Raney Ni reduction of nitrile into primary amine. I either have no reaction or reduction to give a mixture of products. since it is my first time to deal with Raney Ni, I wonder I have not captured some tricks in doing such reduction.
The procedure I use is: weigh a slurry of activated Raney Ni in water, wash with methanol for three times, add in my substrate, stir vigorouly, equip with a H2 balloon, fill the flask with H2 gas, and that's it.
Can anyone give some suggestions to me? thank you!
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discodermolide

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Re: Raney Ni reduction of nitrile
« Reply #1 on: November 08, 2011, 08:27:34 PM »

Hello,

I am new to this forum. Just to say hi to all of you first.
I got trouble with Raney Ni reduction of nitrile into primary amine. I either have no reaction or reduction to give a mixture of products. since it is my first time to deal with Raney Ni, I wonder I have not captured some tricks in doing such reduction.
The procedure I use is: weigh a slurry of activated Raney Ni in water, wash with methanol for three times, add in my substrate, stir vigorouly, equip with a H2 balloon, fill the flask with H2 gas, and that's it.
Can anyone give some suggestions to me? thank you!

Try using a 10% solution of ammonia in methanol. This inhibits the formation of secondary amines.
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orgopete

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Re: Raney Ni reduction of nitrile
« Reply #2 on: November 09, 2011, 01:33:30 AM »

I did one years ago with Raney nickel in a Parr apparatus at fairly high pressure. I ran it at the blow out rupture disk pressure, ~1000 psi? The reduction was slow. I don't remember if I heated it too.
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starfish

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Re: Raney Ni reduction of nitrile
« Reply #3 on: November 09, 2011, 02:40:58 AM »

great! Thanks for advices!!! I now just set up a reaction using 2M NH3 in MeOH as solvent. Hope it will work.
 :P
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