Shen Ying-zhong
2009
Citations
0
Influential Citations
0
Citations
Journal
Fine chemicals
Abstract
A synthetic route of 2-chloro-3-cynaomethylpyridine(Ⅳ) was investigated.First of all,2-chloro nicotinic acid as the initial reactant was chlorinated via SOCl2 in toluene under reflux and then esterified by using methanol to give methyl 2-chloro nicotinate(Ⅰ) in 94% yield.Methyl 2-chloro nicotinate(Ⅰ) was reduced by NaBH4-MeOH in THF at 70 ℃ to produce 2-chloro-3-hydroxylmethyl pyridine(Ⅱ) in 93% yield.2-Chloro-3-hydroxylmethyl pyridine(Ⅱ) then reacted with SOCl2 in dichloromethane at 0 ℃ to give 2-chloro-3-chloromethylpyridine(Ⅲ) in 92% yield.Finally,2-chloro-3-chloromethylpyridine(Ⅲ) was nitrile substituted by using NaCN in DMSO/water system at 100 ℃ to obtain the final product,2-chloro-3-cynaomethylpyridine(Ⅳ),in 86% yield.The overall yield is up to 70%.The intermediates and the target compound were characterized by elementary analysis,FTIR and 1HNMR,respectively.