化工进展

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2-(2,5-二氨基苯)乙醇的合成

尹志刚;陈培同;贾 佳;赵德丰

  

  1. 郑州轻工业学院材料化工学院;大连理工大学精细化工国家重点实验室
  • 出版日期:2007-03-25 发布日期:2007-03-25

Synthesis and structural characterization of 2-(2,5-diamino phenyl)ethanol

YIN Zhigang;CHEN Peitong;JIA Jia;ZHAO Defeng   

  1. School of Materials and Chemical Engineering,Zhengzhou Institute of Light Industry;State Key Laboratory of Fine Chemicals,Dalian University of Technology
  • Online:2007-03-25 Published:2007-03-25

摘要: 在二氯乙烷介质中,将3-氟苯乙酸于70 ℃下硝化4 h得到5-氟-2-硝基苯乙酸(质量分数为67.8%)。用硼烷还原5-氟-2-硝基苯乙酸后,接着用氨水在高压釜中加热到100 ℃氨解,得到2-(5-氨基-2-硝基苯)乙醇(84.4%)。最后,10%Pd/C作催化剂,在无水异丙醇介质中,0.6~0.7 MPa下,于70~80℃催化氢化12 h,得到目标分子2-(2,5-二氨基苯)乙醇(64%)。与文献工艺相比,目标分子总收率提高11%。用H–NMR和MS确定了目标分子2-(2,5-二氨基苯)乙醇的化学结构。

Abstract: Nitration of 3-fluorophenyl acetic acid (1) was accomplished by heating it to 70 ℃ with nitro-sulfuric acid in dichloroethane for 4 h and 5-fluoro-2-nitrophenyl acetic acid (2) was obtained with 67.8% yield. The obtained compound (2) was treated with borane-tetrahydrofuran (B2H6–THF) complex under nitrogen atmosphere in excessive THF for 18 h to give a kind of dark brown oil,followed by ammonolysis with NH3·H2O in autoclave at 100 ℃ for 6 h to produce 2-(5-amino-2- nitrophenyl) ethanol (3) in 84.4% yield. Catalytic hydrogenation of (3) under 0.6~0.7 MPa. over 10% Pd/C in anhydrous isopropyl alcohol at 70~80 ℃ for 12 h produced 2-(2,5-diamino phenyl)ethanol (4) with 64% yield. Compared with the method reported in literature,the overall yield of target molecule (4) was increased by 11%. The chemical structure of (4) was determined by HPLC-MS and 1H-NMR.

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