Sodium hydride → 2-(3-Methoxybenzoyl)-4-oxo-4-pyridin-3-yl-butyronitrile

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Reaction Steps

To 1.3 g (7.5 mmol) of 3-methoxybenzoyl acetonitrile in 30 mL of THF, cooled in a wet ice bath, was added 0.3 g (7.5 mmol) of sodium hydride (60% oil dispersion). After 1 h, added 1.0 g (3.6 mmol) of 3-bromoacetylpyridine hydrobromide. After 3 h, poured the reaction mixture into brine, extracted with ethyl acetate, dried over sodium sulfate, concentrated under reduced pressure and purified by flash chromatography (gradient elution: 40-100% ethyl acetate/hexane) to give 0.95 g (43%) of 2-(3-methoxybenzoyl)-4-oxo-4-pyridin-3-yl-butyronitrile (MH+=295).

Provenance & Evidence