ORGLIST: the problem in reduction of nitrile

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From: Chen Jun (chenjun.net$##$gmail.com)
Date: Thu Jul 07 2005 - 03:55:05 EDT


Hi Everybody:

i attempted to reduce 2-phenyl-3-(pyridin-4-yl)acrylonitrile (CAS No.
[38382-00-2]) to 2-phenyl-3-(pyridin-4-yl)propan-1-amine (CAS No.
[46708-14-9]). i used LiAlH4 (CAS No. [16853-85-3]) as reducing agent
and THF as solvent. However, whatever i tried (elevating temperature
and prolonging reaction time), what i got mainly always was
2-phenyl-3-(pyridin-4-yl)propanenitrile (CAS No. none). The method
used by the only reference involved in this preparation (Journal of
Chemical & Engineering Data 1970, 15(2), 338-) is catalyzed
hydrogenation, which condition is Raney Ni, 2000 psi (about 137 atm)
pressure. But our lab has no this kind of high pressure reaction set.
So, are there any experienced chemist could give me some suggestion
about this reduction?

thanks in advance

chenjun
2005-7-7
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