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Improved Preparation of Tyramine by Curtius Rearrangement
Authors:LI Yun  YANG Fan  XU Xiaoying  PAN Shiyin  WANG Lixin  XIA Chuanqin
Institution:1. Department of Chemistry, Sichuan University, Chengdu, Sichuan 610041, China;2. Key Laboratory of Asymmetric Synthesis & Chirotechnology of Sichuan Province and National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China;3. Tel./Fax: 0086‐028‐85255208
Abstract:An improved and facile preparation of tyramine 2‐(p‐hydroxyphenyl)ethylamine] was described, which starts from phenol and acrylonitrile to form β‐(p‐hydroxyphenyl) propionic acid via Friedel‐Craft's alkylation and nitrile hydrolysis. After hydrazinolysis and a subsequent Curtius rearrangement, tyramine was obtained in 30.2% total yield.
Keywords:preparation  tyramine  β‐(p‐hydroxyphenyl)propionic acid  curtius rearrangement
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