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 concentrated to dryness under high vacuum, treated with water (300 mL) and washed with EtOAc (2×250 mL) to remove the impurities. The pH of the aqueous was adjusted with NaHCO3 to pH˜9-10. The mixture was extracted with DCM (3×300 mL). The combined organics were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography to afford ethyl 4-ethoxy-2-oxo-1,2-dihydropyridine-3-carboxylate (90 g, 66.6% yield).

Provenance & Evidence