Diethyl (ethoxymethylene)malonate → Ethyl 8-fluoro-4-hydroxy-6-methoxyquinoline-3-carboxylate

Participants

Reaction Steps

A mixture of aniline 2-fluoro-4-(methoxy)aniline (22.8 g, 162 mmol) and diethyl [(ethyloxy)methylidene]propanedioate (32.6 mL) were heated to reflux in Dowtherm A under a flow of argon. After 15 minutes (when all ethanol was removed), the mixture was allowed to cool down and was diluted with pentane. A precipitate was formed which was triturated with pentane, filtered and dried under vacuum to afford the product as an oil (33.06 g, 77%); MS (+ve ion electrospray) m/z 265 (M+H)+.

Provenance & Evidence