[CH3:1][O:2][CH:3]([O:8][CH3:9])[CH2:4][CH2:5][CH2:6][NH2:7].C(N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+].[Br:23][C:24]1[CH:33]=[C:32]2[C:27]([C:28](Cl)=[C:29]([N+:34]([O-:36])=[O:35])[CH:30]=[N:31]2)=[CH:26][CH:25]=1>C(Cl)(Cl)Cl.O>[Br:23][C:24]1[CH:33]=[C:32]2[C:27]([CH:28]=[C:29]([N+:34]([O-:36])=[O:35])[C:30]([NH:7][CH2:6][CH2:5][CH2:4][CH:3]([O:8][CH3:9])[O:2][CH3:1])=[N:31]2)=[CH:26][CH:25]=14-Aminobutyraldehyde dimethylacetal (29.41 g, 208.6 mmol), triethylamine (36.36 mL), and potassium carbonate (24.0 g, 173.9 mmol) were added sequentially to a solution of 7-bromo-4-chloro-3-nitroquinoline (50.1 g, 173.9 mmol) in chloroform (200 mL) cooled to 0° C. The reaction was allowed to warm to ambient temperature and was stirred for 4 hours. The reaction mixture was then diluted with water (100 mL) and the reaction was stirred for 10 minutes and the layers were separated. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, and concentrated under reduced pressure to afford 66.9 g of (7-bromo-3-nitroquinolin-yl)(4,4-dimethoxybutyl)amine as a yellow solid.
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