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3104407 
Journal Article 
Synthesis of Methyl 7,9-Dimethyl-5-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carboxylate and Its Analogues 
Vaid, RK; Boini, SK; Alt, CA; Spitler, JT; Hadden, CE; Frank, SA; Moher, ED 
2014 
1 
Synthesis
ISSN: 0039-7881
EISSN: 1437-210X 
46 
18 
2463-2470 
WOS:000342565800008 
A high-yielding five-step synthesis of the title compound, methyl 7,9-dimethyl-5-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carboxylate, starting from 2,4-dimethylaniline was developed. This synthesis involved N-alkylation of 2,4-dimethylaniline with ethyl 4-bromobutyrate to obtain ethyl 4-[(2,4-dimethylphenyl)amino] butanoate. Carbamoylation of the latter followed by hydrolysis of the resulting ester provided 4-[(2,4-dimethylphenyl)(methoxycarbonyl) amino] butanoic acid. Activation of the carboxylic acid using thionyl chloride followed by intramolecular cyclization via a Friedel-Crafts reaction using aluminum trichloride provided the title compound in good yield. Analogues of the title compound were also prepared similarly. 
alkylation; carbamoylation; hydrolysis; Friedel-Crafts reaction