Dimethylformamide → Methyl 1-(4-fluorophenyl)-6-oxo-1,6-dihydropyridine-3-carboxylate

Participants

Reaction Steps

A 250 mL round-bottomed flask was charged with (Z)-dimethyl 4-(methoxymethylene)pent-2-enedioate (2.70 g, 13.5 mmol) and 50 mL of DMF. 4-fluorobenzenamine (1.43 ml, 14.8 mmol) was added dropwise at rt. After stirring at rt for 15 min, the yellow mixture was heated to reflux overnight. The reaction was then diluted with water (200 mL) and extracted with ether (3×100 mL). The combined extracts were dried with MgSO4 and concentrated to give a solid. Purification by MPLC gave methyl 1-(4-fluorophenyl)-6-oxo-1,6-dihydropyridine-3-carboxylate as a slightly yellow solid.

Provenance & Evidence