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 and the residue treated with water (300 mL). The mixture was extracted 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 CH2Cl2 (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