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

Participants

Reaction Conditions

Reaction Steps

The title compound was prepared similarly to literature procedure (Caliendo, G; et. al.; Bioorg. Med Chem. Lett., 2002, 10, 2663), but in one step. Commercially available 3-amino-4-hydroxybenzonitrile (2.5 g, 18.6 mmol) was dissolved in chloroform (300 mL) and saturated sodium bicarbonate (90 mL). The biphasic reaction mixture was cooled to 0° C. and bromoacetyl bromide (2.4 mL, 28 mmol) was added dropwise. The reaction was stirred overnight at room temperature. The layers were separated and the aqueous layer was filtered to yield the desired product as a tan solid, 2.3 g (69%).

Provenance & Evidence