Dicyclohexylcarbodiimide → 4-(2-Chlorophenyl)-3-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylcarbonyl)amino-6,8-dimethylquinoline

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (1.34 g) in dichloromethane (100 ml) was dropwise added DCC (945 mg) under stirring at a temperature of 0° C. The mixture was stirred at 0° C. for 15 minutes, and 3-amino-4-(2-chlorophenyl)-6,8-dimethylquinoline (1.04 g) was added thereto. Thus resulting mixture was further stirred at 0° C. for an hour and at room temperature for one night. The reaction mixture was filtered and the filtrate was concentrated. The residue was purified by a silica gel column chromatography with hexane-ethyl acetate (8:2,V/V), and then crystallized from acetone to give 4-(2-chlorophenyl)-3-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylcarbonyl)amino-6,8-dimethylquinoline (341 mg, 18.0%) as colorless prisms.

Provenance & Evidence