Ethyl bromoacetate → 6-Nitro-2H-1,4-benzoxazin-3(4H)-one

Participants

Reaction Steps

To a stirred suspension of KF (4.9 g, 84.35 mmol) in DMF (25 mL) was added ethyl bromoacetate and the mixture was stirred at rt. After 25 minutes, to the mixture was added 2-amino-4-nitrophenol (5 g, 32.44 mmol) and the mixture was stirred at 60° C. After 25 h, the mixture was cooled to rt, poured into cold brine (200 mL), extracted with EtOAc (100 mL×3). The combined organics were washed with brine (200 mL×1), dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was suspended in MeOH, filtered, and washed the solid with MeOH to give 6-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one as a brown solid: Spectrum (ESI) m/e=193.0 (M+1).

Provenance & Evidence