Diethyl (ethoxymethylene)malonate → ETHYL 7-FLUORO-4-HYDROXY-6-METHOXYQUINOLINE-3-CARBOXYLATE

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-fluoro-4-methoxyaniline (3.00 g, 21.26 mmol) and diethyl ethoxymethylene malonate (4.59 g, 21.26 mmol) is heated at 110° C. for 1 hour then cooled to room temperature. Hexane is added and the solids collected by filtration. This material is suspended in 45 mL of a 3:1 mixture of diphenyl ether:biphenyl and the mixture is heated at reflux for 2 hours to provide a brown solution. The reaction mixture is cooled to room temperature and hexane is added. The resultant solid is collected by filtration washing with hexane to provide 2.62 g of ethyl 7-fluoro-6-methoxy-4-oxo-1,4-dihydro-3-quinolinecarboxylate as a white solid, mp>300° C.

Provenance & Evidence