Document Detail


Short Synthesis of Ethyl 3-(3-aminophenyl)propanoate.
MedLine Citation:
PMID:  21989585     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
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.
Authors:
Ulrike Nagel; Gregor Radau; Andreas Link
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-10-12
Journal Detail:
Title:  Archiv der Pharmazie     Volume:  -     ISSN:  1521-4184     ISO Abbreviation:  -     Publication Date:  2011 Oct 
Date Detail:
Created Date:  2011-10-12     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0330167     Medline TA:  Arch Pharm (Weinheim)     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Copyright Information:
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Affiliation:
Institute of Pharmacy, Ernst-Moritz-Arndt-University Greifswald, Greifswald, Germany.
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