溴保护法合成4-甲氧基-2-吲哚酮工艺研究  

STUDY ON THE SYNTHESIS OF 4-METHOXY-2-INDOLINONE BY BROMO-PROTECTION APPROACH

作　　者：刘长春[1] 陈群[1] 程进[1] 刘承先[1] Liu Changchun;Chen Qun;Cheng Jin;Liu Chengxian(College of Chemistry and Materials Engineering,Changzhou Institute of Engineering and Technology,Changzhou 213164,Jiangsu,China)

机构地区：[1]常州工程职业技术学院化学与材料工程学院,江苏常州213164

出　　处：《精细石油化工》2018年第5期32-36,共5页Speciality Petrochemicals

基　　金：江苏高校品牌专业建设工程资助项目(项目编号PPZY2015B178);江苏省高校优秀中青年教师和校长境外研修计划资助

摘　　要：将溴保护法应用到4-甲氧基-2-吲哚酮合成中,以间甲氧基苯胺为原料,经一锅法溴化、Sandmeyer异亚硝基乙酰替苯胺合成法制备得5,7-二溴-4-甲氧基靛红后,再经钯碳加氢脱溴、水合肼一锅法还原反应制备得目标产物,总收率达54.14%。考察了溴化反应溴素用量、Sandmeyer反应过程反应温度和反应时间对收率的影响,所有产物结构均通过~1H NMR、^(13) C NMR、元素分析等进行了表征。结果表明,溴化反应中甲氧基苯胺与溴素的较佳摩尔比为1∶2.2,Sandmeyer反应适宜的反应条件为80℃反应2h。The bromine protection method was applied to the synthesis of 4-methoxy-2-indolinone with m-methoxyaniline as raw material.5,7-Dibromo-4-methoxyisatin was prepared by one-pot Bromination and Sandmeyer Isonitrosoacetanilide Isatin Synthesis,followed by palladium carbon hydrogenation of bromine and hydrazine hydrate one-pot reduction to give 4-methoxy-2-indolinone with the total yield of 54.14%.The effects of dosage of bromine,Sandmeyer reaction＇s temperature and time on the yield were investigated.All products＇ structures were characterized by ^1 H NMR,^13 CNMR and elemental analysis.The result shows that the optimized molar ratio of m-methoxyaniline to bromine was 1∶2.2 in the bromination reaction and the optimum Sandmeyer reaction condition is 80℃for 2 h.

关 键 词：溴保护法 4-甲氧基靛红 4-甲氧基-2-吲哚酮 Sandmeyer异亚硝基乙酰替苯胺合成法 一锅法 

分 类 号：TQ251.3[化学工程—有机化工]