[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].Cl[C:10](Cl)(Cl)[CH:11]([OH:13])O.Cl.[NH2:17][OH:18].S([O-])([O-])(=O)=O.[Na+].[Na+].Cl>O>[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:11](=[O:13])[CH:10]=[N:17][OH:18]To a 1000 mL round bottom flask, 2-bromoaniline (15 g, 0.0872 mol), water (400 mL), chloral hydrate (17.05 g, 0.1046 mol), hydroxylamine hydrochloride (19.25 g, 0.279 mol) and sodium sulfate (57.81 g) were added. To this reaction mixture conc. HCl (21 mL) was slowly added. The reaction mixture was stirred at 100° C. for 3 h. The white precipitate was formed and was collected by filtration. The white solid was dried to get the title compound [7 g, 33%]. 1HNMR (300 MHz, DMSO-d6): δ 12.46 (s, 1H), 9.48 (s, 1H), 7.89 (d, J=8.1 Hz, 1H), 7.69 (d, J=8.1 Hz, 1H), 7.66 (s, 1H), 7.42 (t, J=6.9 Hz, 1H), 7.15 (t, J=7.5 Hz, 1H); LC-MS (ESI): Calculated mass: 241.9; Observed mass: 243.0 [M+H]+ (RT: 0.66 min).
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