Triethylamine → Ethyl 4-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate

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Reaction Steps

Triethylamine (7.07 mL, 50.7 mmol) was added to a suspension of 4-hydroxy-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid ethyl ester (10.0 g, 50.7 mmol) and POCl3 (27.85 mL, 304.3 mmol). After stirring 16 hours, the reaction mixture was concentrated under reduced pressure. The resulting residue was poured onto ice, carefully neutralized with saturated K2CO3 solution, and diluted with EtOAc. The layers were separated and the aqueous phase further extracted with EtOAc. The combined organic extracts were dried (MgSO4) and concentrated under reduced pressure to yield 7.3 g (67%) clean desired product.

Provenance & Evidence