2,4-Octanedione → 4-(3,4-Dimethoxyphenyl)-6,7-dimethoxy-2-methyl-3-valerylquinoline

Participants

Reaction Steps

A mixture of 2-amino-3',4',4,5-tetramethoxybenzophenone hydrochloride (25.0 g), 2,4-octanedione (10.5 g) and ethanol (500 ml) was stirred under reflux for 2 hours. The solvent was evaporated under reduced pressure. The residue was poured into saturated aqueous sodium bicarbonate solution, and extracted with chloroform. The chloroform layer was washed with water and dried over magnesium sulfate. The chloroform was evaporated, and the residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform-ethanol (20:1, v/v) gave 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-methyl-3-valerylquinoline- This compound was recrystallized from ethanol to give colorless prisms. mp. 119°-120° C.

Provenance & Evidence