Improved Preparation of Tyramine by Curtius Rearrangement

Improved Preparation of Tyramine by Curtius Rearrangement

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,...

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Veröffentlicht in:Chinese journal of chemistry 2009-02, Vol.27 (2), p.433-436
Hauptverfasser: LI, Yun, YANG, Fan, XU, Xiaoying, PAN, Shiyin, WANG, Lixin, XIA, Chuanqin
Format: Artikel
Sprache:eng
Schlagworte:
curtius rearrangement
preparation
tyramine
β-(p-hydroxyphenyl)propionic acid
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Zusammenfassung: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. An improved and facile preparation of tyramine [2‐(p‐hydroxyphenyl)ethyl‐ amine] 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.
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.200990072