2-Methoxyethanol → 1,4-Dihydro-7-(2-methoxyethoxy)-4-oxo-3-quinolinecarbonitrile

Participants

Reaction Steps

A mixture of sodium hydride (500 mg, 12.5 mmol) and 7-fluoro-4-hydroxyquinoline-3-carbonitrile (1.30 g, 6.9 mmol) in 2-methoxyethanol (30 mL) is heated at reflux overnight. Additional sodium hydride (250 mg, 6.25 mmol) is added and the reaction mixture is heated at reflux overnight. Additional sodium hydride (250 mg, 6.25 mmol) is added and the reaction mixture is heated at reflux for 8 hours. The reaction mixture is cooled to room temperature and partitioned between ethyl acetate and saturated sodium bicarbonate. The basic layer is acidified with aqueous HCl and the resultant solid is collected by filtration to provide 1.05 g of 7-(2-methoxyethoxy)-4-oxo-1,4-dihydroquinoline-3-carbonitrile as a white solid, mp>250° C.

Provenance & Evidence