Acetic Acid → Ethyl 4-Ethoxy-2-oxo-1,2-dihydropyridine-3-carboxylate

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Reaction Steps

A mixture of ethyl 2-cyano-5-(dimethylamino)-3-ethoxypenta-2,4-dienoate (150 g, 0.63 mol) and HOAc (600 mL) was refluxed overnight. The mixture was cooled to RT, concentrated to dryness, treated with water and washed with EtOAc (2×). The aqueous layer was made basic (pH=9-10) with NaHCO3, extracted with DCM (3×) and the combined organics were washed with brine, dried over Na2SO4, concentrated and purified by silica gel chromatography to afford ethyl 4-ethoxy-2-oxo-1,2-dihydropyridine-3-carboxylate (90 g, 67% yield).

Provenance & Evidence