Acetic Acid → HCID 13785765, compound

Participants

Reaction Steps

A solution of 3-[(2-aminophenyl)amino]-2-butenoic acid, methyl ester (2.50 g., 12.0 mmole) in anhydrous tetrahydrofuran (12 ml.) is treated with 2-(trifluoromethyl)benzaldehyde (1.74 g., 10.0 mmole) and acetic acid (0.2 ml.). The resulting reaction mixture is stirred at room temperature under argon for 24 hours. The solvent is removed and the resulting yellow solid is triturated with isopropyl ether to give 3.27 g. of an off-white product. Recrystallization from dichloromethane-isopropyl ether gives 2.39 g. of 2,5-dihydro-4-methyl-2-2-(trifluoromethyl)phenyl]-1H-1,5-benzodiazepine-3-carboxylic acid, methyl ester; m.p. 190°-192°. TLC (silica gel; acetone:hexanes, 35:65) Rf =0.47.

Provenance & Evidence