2,6-Dichlorobenzaldehyde → HCID 13785763, compound

Participants

Reaction Steps

A solution of 3-[(2-aminophenyl)amino]-2-butenoic acid, methyl ester (4.74 g., 230 mmole) in anhydrous tetrahydrofuran (20 ml.) and acetic acid (0.2 ml.) is treated with 2,6-dichlorobenzaldehyde (4.03 g., 23.0 mmole). The resulting reaction mixture is stirred at room temperature for 4 days. The solvent is stripped off to give a brown oil which is dissolved in isopropyl ether and allowed to stand at 0°-5° (refrigerator) for 24 hours. The solid that precipitates is filtered off and washed with additional isopropyl ether. This product is triturated with isopropyl ether and filtered off to give 2-(2,6-dichlorophenyl)-2,5-dihydro-4-methyl-1H-1,5-benzodiazepine-3-carboxylic acid, methyl ester; 119°-120° (with decomposition). TLC (silica gel; ethyl acetate:hexanes, 40:60) Rf =0.38.

Provenance & Evidence