2-氯-3-氰甲基吡啶的合成及表征  

Synthesis and Characterization of 2-Chloro-3-cyanomethylpyridine

作　　者：李月琴[1] 陶弦[1] 徐慧华[1] 沈应中[1] 

机构地区：[1]南京航空航天大学材料科学与技术学院应用化学系,江苏南京210016

出　　处：《精细化工》2009年第9期928-931,共4页Fine Chemicals

基　　金：江苏省自然科学基金(BK2007199)~~

摘　　要：对2-氯-3-氰甲基吡啶(Ⅳ)的合成进行了研究。首先,起始原料2-氯烟酸和SOCl2在甲苯中回流酰化,再加入甲醇酯化,得到2-氯烟酸甲酯(Ⅰ),产率94%。Ⅰ在NaBH4-MeOH/THF还原体系中,于70℃反应生成2-氯-3-羟甲基吡啶(Ⅱ),产率93%。Ⅱ和SOCl2在二氯甲烷中,0℃反应生成2-氯-3-氯甲基吡啶(Ⅲ),产率92%。最后,Ⅲ和NaCN在DMSO和水体系中,100℃时发生氰基取代,生成2-氯-3-氰甲基吡啶(Ⅳ),产率86%。该合成路线的总收率达70%。中间产物和目标化合物经元素分析,FTIR和1HNMR进行了表征。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 SOC12 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.

关 键 词：2-氯烟酸 NaBH4-MeOH还原 氰基取代 2-氯-3-氰甲基吡啶 

分 类 号：O626.32[理学—有机化学]