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A mixture of 0.5 g of 4-chloro-6,7-dimethoxy-3-quinolinecarbonitrile, 0.51 g of 3-chloroaniline, 0.16 ml of pyridine, and 6 ml of ethoxyethanol was stirred under nitrogen, at reflux temperature for 6 h. The mixture was cooled and partitioned with dichloromethane and aqueous sodium bicarbonate. The organic layer was washed with water, dried and evaporated. The residue was recrystallized from ethyl acetate-hexanes to give 0.37 g of 4-[(3-chlorophenyl)amino]-6,7-dimethoxy-3-quinolinecarbonitrile as a solid, mp 214-217° C.

1. temperatureat reflux temperature for 6 h
2. temperatureThe mixture was cooled
3. custompartitioned with dichloromethane and aqueous sodium bicarbonate
4. washThe organic layer was washed with water
5. customdried
6. customevaporated
7. customThe residue was recrystallized from ethyl acetate-hexanes