9-乙基四氢咔唑的合成工艺研究  

Synthesis of 9-Ethyl Tetrahydro-carbazole

作　　者：洪海燕[1] 张伟[1] 鲁墨弘[1] 李明时[1] 单玉华[1] 

机构地区：[1]常州大学石油化工学院,江苏常州213164

出　　处：《精细化工》2016年第1期117-120,共4页Fine Chemicals

基　　金：国家自然科学基金(21307009)~~

摘　　要：该文以苯肼、环己酮为起始原料,经醋酸环化合成四氢咔唑,收率达70.5%,再与溴乙烷经烷基化反应制得9-乙基四氢咔唑。产物的结构经~1HNMR和^(13)CNMR表征。经单因素实验考察,确定合成9-乙基四氢咔唑的最优条件为:n(四氢咔唑)∶n(溴乙烷)∶n(氢氧化钠)=1∶4∶1.5,m(四氢咔唑)∶m(碘化钾)=1∶0.01,c(四氢咔唑)=0.50 mol/L,c(十六烷基三甲基溴化铵)=2.5×10^(-3)mol/L,乙腈为溶剂,回流反应9 h,收率为86.0%。该路线与传统工艺(环己酮先经氯化再与N-乙基苯胺缩合)相比,可避免氯化副产物生成,反应易控制,更适合工业生产。Tetrahydro-carbazole was synthesized by cyclization reaction of phenyl-hydrazine and cyclohexanone with the yield of 70. 5%. And 9-ethyl tetrahydro-carbazole was synthesized by alkylation of tetrahydro-carbazole with ethyl bromide. The structures of product were characterized by1 HNMR and^（13）CNMR. The optimum reaction conditions for synthesis of 9-ethyl tetrahydro-carbazole were as follows：n（ tetrahydro-carbazole） ∶ n（ ethyl bromide） ∶ n（ sodium hydroxide） = 1∶4∶1. 5,m（ tetra-hydro-carbazole）∶ m（ potassium iodide） = 1 ∶ 0. 01,c（ hexadecyl trimethyl ammonium bromide） = 2. 5 × 10^（-3）mol / L,c（ tetrahydro-carbazole） = 0. 50 mol/L. The yield of 9-ethyl tetrahydro-carbazole was 86. 0% under the optimum conditions in the solvent of acetonitrile for 9 h. Compared with the traditional process（ chlorination of cyclohexanone with chlorine,followed by condensation）,the synthesis could avoid the formation of chlorinated by-products and was easily to be commercialized.

关 键 词：四氢咔唑 溴乙烷 9-乙基四氢咔唑 相转移催化剂 精细化工中间体 

分 类 号：O626.13[理学—有机化学]