Dimethyl Sulfate → Ethyl 7-fluoro-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate

Participants

Reaction Steps

A mixture of ethyl 7-fluoro-4-hydroxyquinoline-3-carboxylate (4.7 g), anhydrous potassium carbonate (3.0 g), dimethyl sulphate (2.52 g) and butanone (200 ml) was boiled under reflux for 14 hours. The solvent was evaporated and the residue was triturated with dichloromethane (150 ml). The mixture was filtered and the filtrate was evaporated to a small volume. Diethyl ether was added, causing a solid to precipitate. The solid was collected, washed with ether, dried and recrystallised from IMS to give the novel compound ethyl 7-fluoro-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate, m.p. 164°-166°.

Provenance & Evidence