Sodium ethoxide → 1,6-Naphthyridin-2(1H)-one, 5,8-dimethyl-

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Reaction Conditions

Reaction Steps

A mixture of (E)-ethyl 3-(4-amino-2,5-dimethylpyridin-3-yl)acrylate (5 g, 22.7 mmol) and sodium ethanolate (6.2 g, 91 mmol) in ethanol (100 mL) was heated to 80° C. for 2 h. The reaction mixture was concentrated and diluted with water (50 mL). The aqueous phase was extracted with EtOAc (100 mL×3), and the combined organic layers were washed with saturated sodium chloride solution, dried with sodium sulfate, and concentrated to give 2.3 g of the product as a yellow solid. MS (ESI): m/z 175.1 [M+H]+.

Provenance & Evidence