Diethyl 2-[(4-fluoroanilino)methylene]malonate → Ethyl 6-fluoro-4-hydroxyquinoline-3-carboxylate

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Reaction Steps

2-[(4-Fluoro-phenylamino)-methylene]-malonic acid diethyl ester (11.5 g, 40.9 mmol)) was added in portions to hot diphenylether (80 mL), while heating at reflux. The resultant mixture was heated an additional 2 hours, then allowed to cool to room temperature. A solid white precipitate developed. The mixture was diluted with heptanes, and the product was collected by filtration, washed with heptane, to give the product as a colorless crystalline solid, 3.0 g (31%). MS: m/z 235.9 (MH+).

Provenance & Evidence