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Short Synthesis of Ethyl 3‐(3‐aminophenyl)propanoate
Author(s) -
Nagel Ulrike,
Radau Gregor,
Link Andreas
Publication year - 2011
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.200900164
Subject(s) - chemistry , propanoic acid , knoevenagel condensation , ethanol , chloride , carboxylic acid , ethyl formate , organic chemistry , nucleophile , formate , medicinal chemistry , catalysis
Abstract A short and effective synthesis of ethyl 3‐(3‐aminophenyl)propanoate is presented, employing a tandem Knoevenagel condensation/alkylidene reduction of 3‐nitrobenzaldehyde with Meldrum's acid in TEAF (triethylammonium formate) followed by reduction of the intermediate 3‐(3‐nitrophenyl)propanoic acid by stannous chloride in ethanol. The use of stannous chloride as the reducing agent in ethanol enabled the simultaneous esterification of the carboxylic acid. Thus, stannous chloride was acting simultaneously as a Lewis acid, which activates the carboxylic acid towards a nucleophilic attack by ethanol.