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

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Reaction Steps

A solution of 2-Amino-4-nitro phenol (6.0 g, 38.93 mmol) in methylene chloride (200 ml) was cooled to 0° C. Triethyl amine (16.3 ml, 116.9 mmol) was added followed by chloroacetyl chloride (3.42 ml, 42.8 mmol) portionwise. The mixture was stirred at room temperature for 18 hours, then diluted with methylene chloride. The organic phase was washed with water, dried over MgSO4, filtered and concentrated under reduced pressure to give 7.5 g of 6-nitro-4H-benzo[1,4]oxazin-3-one as a solid, 100%.

Provenance & Evidence