[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].C(=O)(O)[O-].[Na+].Cl[CH2:18][C:19](Cl)=[O:20]>C(Cl)(Cl)Cl.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[N+:8]([C:6]1[CH:5]=[CH:4][C:3]2[O:11][CH2:18][C:19](=[O:20])[NH:1][C:2]=2[CH:7]=1)([O-:10])=[O:9]A suspension of 2-amino4-nitrophenol (7.7 g, 50 mmol) was prepared in 125 mL chloroform. To this suspension was added benzyltriethylammonium chloride (11.4 g, 50 mmol) and sodium bicarbonate (16.80 g, 200 mmol) and the suspension cooled in an ice bath. A solution of chloroacetyl chloride (4.8 mL, 60 mmol) in chloroform (10 mL) was added. The solution was stirred overnight at room temperature, then refluxed for 3 hours and again let sit overnight at room temperature. The solvent was removed under vacuum and water was added to the residue. The solid was filtered, washed with water, and recrystallized from ethanol. The recrystallized solid was filtered and washed with cold ethanol and then dried, to yield 6-nitro-4-H-benzo[1,4]oxazin-3-one as a solid product. Some additional product precipitated from the ethanol filtrate as a second crop and was recovered by filtration.
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