[O-]S(S([O-])=O)=O.[Na+].[Na+].[Br:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([NH:23][CH2:24][CH:25]([CH3:27])[CH3:26])=[C:15]([N+:20]([O-])=O)[CH:16]=[N:17]2)=[CH:12][CH:11]=1>O.C(O)(C)C>[Br:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([NH:23][CH2:24][CH:25]([CH3:27])[CH3:26])=[C:15]([NH2:20])[CH:16]=[N:17]2)=[CH:12][CH:11]=1A solution of Na2S2O4 (193 g) in H2O (1 L) was added to a boiling solution of (7-bromo-3-nitroquinolin-4-yl)isobutylamine (32.0 g, 99 mmol) in isopropanol (1 L). Upon complete addition, the reaction mixture was cooled to room temperature and the bulk of the isopropanol was removed on a rotary evaporator. The resulting mixture was extracted with CH2Cl2 (3×), and the combined organic layers were dried over Na2SO4, filtered, and concentrated to afford 39.5 g of the crude 7-bromo-N4-isobutylquinoline-3,4-diamine as a yellow solid.
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