Dimethylformamide → 3,4-Dihydro-7-hydroxy-4-[2-(3,4-dimethoxyphenyl)ethyl]-1,4-benzoxazine-3-one

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Reaction Steps

A solution of the amide (0.50 mmol) was added to a mixture of sodium hydride (2.3 mmol) and dimethyl formamide (2.0 ml). After stirring for 30 min a solution of 1-bromo-2-(3,4-dimethoxyphenyl)ethane (0.50 mmol) in dimethyl formamide (1.0 ml) was added at 0° C. After 2 h an aqueous workup with ethyl acetate was performed. The organic layers were dried with magnesium sulfate and concentrated. Purification by flash chromatography provided the title compound.

Provenance & Evidence