Chloroacetyl chloride → 7-nitro-3,4-dihydro-2H-1,4-benzoxazin-3-one

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Reaction Steps

This compound was prepared by General Method 1 from 2-amino-5-nitrophenol (6.0 g, 39 mmol), NaHCO3 (7.8 g, 93 mmol), and chloroacetyl chloride (3.58 mL, 45 mmol) to afford 6.91 g (91%) of 7-nitro-2H-1,4-benzoxazin-3(4H)-one. Data for 7-nitro-2H-1,4-benzoxazin-3(4H)-one: Rf 0.44 (11.5:1 CH2Cl2:MeOH); 1H NMR (400 MHz, DMSO-d6) δ 11.3 (br s, 1H), 7.90 (dd, 1H, J=8.7, 2.6), 7.76 (d, 1H, J=2.5), 7.06 (d, 1H, J=8.7), 4.73 (s, 2H).

Provenance & Evidence