title: Short synthesis of ethyl 3-(3-aminophenyl)propanoate.
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.
authors: Institute of Pharmacy, Ernst-Moritz-Arndt-University Greifswald, Germany. link@uni-greifswald.de
authors: Ulrike
authors: U
authors: Nagel
authors: Gregor
authors: G
authors: Radau
authors: Andreas
authors: A
authors: Link
mesh_terms: D002264:Carboxylic Acids / Q000138:chemical synthesis; D004951:Esterification; D000431:Ethanol / Q000737:chemistry; D010666:Phenylpropionates / Q000138:chemical synthesis*; D011407:Propane / Q000138:chemical synthesis*
chemical_list: D002264:Carboxylic Acids; D010666:Phenylpropionates; C571051:ethyl 3-(3-aminophenyl)propanoate; D000431:Ethanol; D011407:Propane