1-苯基吲哚的合成  

Synthesis of 1-phenylindole

作　　者：冯筱晴[1,2] 唐龙[1] 王瑞瑞[1] 王羚竹[1] 宋国强[1] 

机构地区：[1]常州大学制药与生命科学学院,江苏常州213164 [2]常州市药品制造与质量控制工程重点实验室,江苏常州213164

出　　处：《化工进展》2013年第10期2486-2490,共5页Chemical Industry and Engineering Progress

基　　金：江苏省产学研前瞻性联合研究项目(BY-2013024-20);江苏省研究生科研创新计划(CXZZ12_0730);江苏省高等学校大学生创新创业训练计划(201310292005Z)项目

摘　　要：以二苯胺和乙二酰氯为起始原料经偶联、酰化、还原反应得到1-苯基吲哚,并探索了其影响因素。结果表明合成中间体N,N-二苯基-2-氯-2-氧代乙酰胺的较佳条件为:n(二苯胺):n(乙二酰氯)=1∶3,反应温度20～25℃,反应2.5 h,收率98.02%,HPLC纯度97.68%;产品1-苯基靛红的较优合成工艺条件为:n(N,N-二苯基-2-氯-2-氧代乙酰胺):n(无水AlCl3)=1∶3,反应温度10℃,反应时间2 h,收率86.76%,HPLC纯度98.45%;目标产物1-苯基吲哚的最佳工艺条件为:n(1-苯基靛红):n(硼氢化钠)=1∶3,n(1-苯基靛红):n(氯化锌)=1∶0.05,反应温度110℃,反应时间12 h,收率72.41%,HPLC纯度98.14%。产品及中间体结构经1H NMR、MS和显微熔点仪分析表征确认。In this paper,n-phenylaniline and oxalyl chloride were used to prepare 1-phenylindole. The experimental conditions,such as material ratio,reaction time,the amount of catalyst and so on were investigated. The optimal conditions of the coupling reaction were found as：n（n-phenyl -aniline）∶n（oxalyl chloride）=1∶3,reaction temperature 20-25 ℃,reaction time 2.5 h,under which the yield of 1-（diphenylamino）-2-chloro-ethanedione was up to 98.02%based on n-phenyl-aniline and the purity was 97.68%as determined by HPLC. The best reaction conditions for preparing 1-phenyl isatin were found as：n（1-（diphenylamino）-2-chloro-ethanedione）∶n（Anhydrous AlCl3）=1∶3,reaction temperature 10 ℃, reaction time 2 h,under which the yield of 1-phenylisatin was 86.76% based on 1-（diphenylamino）-2-chloro-ethanedione and the purity was 98.45% as determined by HPLC. The reduction reaction conditions were optimized as：n（1-phenylisatin）∶n（sodium borohydride） = 1∶3,n（1-phenylisatin）∶n（zinc chloride）=1∶0.05,reaction temperature 110 ℃,reaction time 12 h,under which the yield of 1-phenylisatin was 72.41%based on 1-phenylisatin and the purity was 98.14%as determined by HPLC. The structures of the product were identified by 1H NMR,MS and Micro melting point instrument.

关 键 词：二苯胺 N N-二苯基-2-氯-2-氧代乙酰胺 1-苯基靛红 1-苯基吲哚 合成 

分 类 号：TQ246.7[化学工程—有机化工]