4,6-二氯吲哚的合成工艺研究  

Study on the Synthesis Process of 4,6-Dichloroindole

作　　者：唐文强 赖普辉[1,2] 高艳蓉 仝红娟 吴文莉 TANG Wen-qiang;LAI Pu-hui;GAO Yan-rong;TONG Hong-juan;WU Wen-li(School of Pharmacy,Shaanxi Institute of International Trade&Commerce,Shaanxi Xi’an 712046,China;Co-Innovation Center of Shaanxi Green Manufacturing Technology of Traditional Chianese Medicine,Shaanxi Xi’an 712046,China)

机构地区：[1]陕西国际商贸学院医药学院,陕西西安712046 [2]陕西省中药绿色制造技术协同创新中心,陕西西安712046

出　　处：《当代化工》2019年第7期1405-1407,1411,共4页Contemporary Chemical Industry

基　　金：陕西省高校科协青年人才托举计划项目,项目号:20180312;陕西省大学生创新创业训练计划项目,项目号:201849003

摘　　要：以3,5-二氯苯胺、盐酸羟胺和水合氯醛为原料,经桑德迈尔异亚硝基乙酰替苯胺法制备得4,6-二氯靛红,再经硼氢化钠/三氟化硼乙醚还原制备得4,6-二氯吲哚。考察了酰化反应温度和反应时间,环化反应温度、还原剂用量对反应的影响,并采用FT-IR、^1H NMR、^13C NMR和ESI-MS对产物4,6-二氯吲哚的结构进行了表征。研究结果表明,制备4,6-二氯吲哚较佳的酰化反应温度为100℃(回流温度)、时间0.5 h;环化反应温度为85℃,还原剂用量为(三氟化硼乙醚)/n(4,6-二氯靛红)=2.4/1,n(硼氢化钠)/n(4,6-二氯靛红)=2.6/1。4,6-Dichloro-1 H-indole was prepared from 3,5-dichloraniline, hydroxylamine hydrochloride and chloral hydrate by Sandmeyer isonitrosoacetanilide isatin synthesis method, and then it was reduced to 4,6-dichloro-1 H-indole through NaBH4/BF3-Et2O reduction system. The effect of acetylation reaction time and temperature, cyclization reaction temperature and the amount of reducing agents on the yield of product was researched. The target product was characterized by FT-IR,^1H NMR,^13C NMR and ESI-MS. The research results showed that the optimized acetylation temperature and time for preparing 4,6-dichloro-1 H-indole were 100℃ and 0.5 h;suitable cyclization temperature was 85 ℃;the amount of reducing agents were n(boron fluoride ethyl ether)/n(4,6-dichloro-1 H-indole-2,3-dione)=2.4/1, n(sodium borohydride)/n(4,6-dichloro-1 H-indol-e-2,3-dione)=2.6/1.

关 键 词：4 6-二氯吲哚 3 5-二氯苯胺 4 6-二氯靛红 还原反应 

分 类 号：TQ031.2[化学工程]