Sodium hydride → methyl 3,4-dihydro-2-isopropyl-3-oxo-2H-1,4-benzoxazine-4-acetate

Participants

Reaction Steps

To a solution of 2-isopropyl-2H-1,4-benzoxazin-3(4H)-one (19.1 g) in N,N-dimethylformamide (200 ml), sodium hydride (60% in oil, 4.0 g) was added and stirred at room temperature for 30 minutes, to which a solution of methyl bromoacetate (10 ml) in N,N-dimethylformamide (200 ml) was added dropwise with ice-cooling. After stirring with ice-cooling for 1 hour, the reaction mixture was diluted with water and subjected to extraction with ethyl acetate. The extract was washed with water, dried (MgSO4) and evaporated to dryness, to give methyl 3,4-dihydro-2-isopropyl-3-oxo-2H-1,4-benzoxazine-4-acetate as an oil. Yield was 26.0 g (98.9%).

Provenance & Evidence