Author Topic: Reductive amination of aldehydes  (Read 155 times)

Tsathoggua

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Reductive amination of aldehydes
« on: July 07, 2010, 01:43:04 PM »
Quick question:

Can borohydride or Al/Hg be used for reductive amination of aldehydes to primary amines using NH3/hydroxylamine as amine source?

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jon

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Re: Reductive amination of aldehydes
« Reply #1 on: July 08, 2010, 03:25:35 AM »
i don't see why not in the case of borohydrides i would use ammonium acetate and a little excess acetic to achieve ph 6 to get a better equilibrium to the shiff's base since aldehydes are more reactive you would want to drive the equilibrium to the right by buffering the ammonia or hydroxylamine with acetic acid since the optimal elimination of water from zie carbinol is obtained at ph range 6 acetic acid buffers these two nicely other wise you just have the ammonia bouncing back and forth as the carbinol/aldehyde rather then forming the more stable shiff's base.
also as the reaction progresses  the solution would become increasingly basic so this would mean you would have to attend to the ph of the system.
being more reactive i suspect the reduction rate of the aldehyde occurs more rapidly .
« Last Edit: July 08, 2010, 04:24:41 AM by jon »

Tsathoggua

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Re: Reductive amination of aldehydes
« Reply #2 on: July 08, 2010, 02:40:59 PM »
Reccomend going via the aldoxime maybe? less fiddling about with PH control.

Which route is likely to have better yields?

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jon

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Re: Reductive amination of aldehydes
« Reply #3 on: July 10, 2010, 07:00:56 PM »
the aldoxime would work too but you still have to buffer it with acetic acid.