Chloroacetyl chloride → 6-Nitro-2H-1,4-benzoxazin-3(4H)-one

Participants

Reaction Steps

Using 2-amino-4-nitrophenol (10 g, 65 mmol), triethylamine (11.7 mL, 84 mmol) and chloroacetyl chloride (5.4 mL, 68 mmol) in THF (150 mL) followed by sodium hydride (5.2 g of a 60% suspension in oil, 130 mmol) to yield the title compound as a grey solid (5 g, 33%). δH (DMSO-d6) 4.78 (2H, s), 7.15 (1H, d, J 8.9 Hz), 7.74 (1H, d, J 2.4 Hz), 7.84 (1H, dd, J 8.9, 2.6 Hz), 11.09 (1H, s).

Provenance & Evidence