| 1-苯基吲哚的合成 |
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| 引用本文： | 冯筱晴,唐龙,王瑞瑞,王羚竹,宋国强.1-苯基吲哚的合成[J].化工进展,2013,32(10):2486-2490. |
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| 作者姓名： | 冯筱晴 唐龙 王瑞瑞 王羚竹 宋国强 |
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| 作者单位： | 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 |
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| 基金项目： | 江苏省产学研前瞻性联合研究项目，江苏省研究生科研创新计划，江苏省高等学校大学生创新创业训练计划(201310292005Z)项目。 |
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| 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。
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| 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 |
Synthesis of 1-phenylindole |
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| FENG Xiaoqing
,
TANG Long
,
WANG Ruirui
,
WANG Lingzhu
,
SONG Guoqiang.Synthesis of 1-phenylindole[J].Chemical Industry and Engineering Progress,2013,32(10):2486-2490. |
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| Authors: | FENG Xiaoqing TANG Long WANG Ruirui WANG Lingzhu SONG Guoqiang |
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| Affiliation: | 1School of Pharmaceutical Engineering ＆Life Science，Changzhou University，Changzhou 213164，Jiangsu，China；2Changzhou’s Key Laboratory of Pharmaceutical Manufacture and Quality Control Engineering，Changzhou 213164，Jiangsu，China |
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| Abstract: | 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. |
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| Keywords: | n-phenylaniline 1-(diphenylamino)-2-chloro-ethanedione 1-phenylisatin 1-phenylin-dole synthesis |
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