Water → 3-Oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbonitrile

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Reaction Conditions

Reaction Steps

3-amino-4-hydroxybenzonitrile (g, 10 mmol was dissolved in acetone (20 mL) and water (20 mL) containing sodium bicarbonate (4 g). 2-chloroacetyl chloride was added slowly and the mixture heated to reflux for 4 h and then allowed to stir overnight at 25 ° C. The layers were separated, and the water layer was extracted with ethyl acetate. The organic layers were combined and evaporated to give 3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-carbonitrile as an oil (1.3 g): 1H NMR (400 M ; DMSO-D6): 7.4 (d, 1H); 7.2 (s, 1H); 7.1 (d, 1H).

Provenance & Evidence