From: liux (liux$##$med.usyd.edu.au)
Date: Mon Aug 30 1999 - 20:45:42 EDT
Here's the summary of answers to my question about synthesis of
4-iodophenethylamine (how to reduce nitrile into amine without taking
Iodine off the aromatic ring?)
1. From: zabicky$##$bgumail.bgu.ac.il (Jacob Zabicky)
n alternative route can be suggested, using nitromethane as synthone for
the CH2NH2 group:
p-I-C6H4CH2-X + CH3NO2 --(base)--> p-I-C6H4CH2-CH2NO2
p-I-C6H4CH2-CH2NO2 ---(H)---> p-I-C6H4CH2-CH2NH2
se for example: G.B. Bachman et al., JACS 76, 3972 (1954).
2. From: Zai-Xin Chen <chenzx$##$online.sh.cn>
I think it is almost impossible to reduce nitrile in presence of
iodine,but I am
not sure.I think you can get the 4-amine-phenethylamine firstly,then
using NaNO2/HCl
to diazo-reaction.Substituting the diazonium using KI,maybe you can get
the TM.
3. From: alihoyer$##$post.uni2.dk
Would diborane do the job?
Thanks for your answers.
Cheers,
Xiang
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