Chloroacetyl chloride → HCID 59817752, compound

Participants

Reaction Conditions

Reaction Steps

At 0° C., a solution of 2-amino-4-nitrophenol (6.24 g, 40.5 mmol) in DMF (62 mL) is treated with K2CO3 (8.44 g, 61.1 mmol) and chloroacetyl chloride (X. Huang, C. Chan, Synthesis 1984, 31, 851.) (3.5 mL, 44.0 mmol), stirred at the same temperature for 40 min, warmed to 60° C., and stirred for 23 h, cooled to 0° C., and treated with KI (1.32 g, 7.95 mmol) and a solution of 1-methoxy-3-(p-toluenesulfonyloxy)propane (12.1 g, 49.5 mmol) in DMF (24 mL). After adding 60% of NaH (2.00 g, 50.0 mmol) over 10 min, the mixture is stirred at 0° C. for 1 h, warmed to 60° C., stirred for 24 h, and treated with H2O (650 mL). After extraction of the mixture with EtOAc (3×80 mL) and Et2O (3×80 mL), the combined org. layer is washed with H2O (2×50 mL), dried (Na2SO4), and evaporated. A SiO2 flash chromatography (300 g, hexane/EtOAc 5:4) gives 4-(3-methoxypropyl)-6-nitro-4H-benzo[1,4]oxazin-3-one as yellow solid.

Provenance & Evidence