ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[C:14]([N+:23]([O-:25])=[O:24])=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][CH:17]=[CH:16]2.C([O-])([O-])=O.[Na+].[Na+].[OH-].[Na+]>C(Cl)(Cl)Cl>[Cl:12][C:13]1[C:14]([N+:23]([O-:25])=[O:24])=[C:15]2[C:20](=[CH:21][CH:22]=1)[N+:19]([O-:9])=[CH:18][CH:17]=[CH:16]2m-Chloroperbenzoic acid (70–75% by wt, 2.7 g, 15.6 mmol) was added in portions to a stirred, ambient temperature solution of 6-chloro-5-nitroquinoline (2 g, 9.6 mmol) in CHCl3 (15 mL). The mixture was stirred for 6 h. After this time, more CHCl3 was added, followed by 30 mL of a saturated aqueous solution of Na2CO3 and 1 mL 1M NaOH. The mixture was separated and the aqueous phase extracted with CHCl3 (×2). The organic phases were combined and washed with a saturated aqueous solution of Na2CO3, H2O and brine. The organic phase was dried (MgSO4) and the solvent removed in vacuo to give 6-Chloro-5-nitroquinoline-N-oxide as a yellow solid (1.8 g, 84%); H (300 MHz; CDCl3) 7.6 (1H, m), 7.7 (1H, d), 7.95 (1H, d), 8.65 (1H, d) and 8.75 (1H, d).
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