Cl.[CH3:2][NH:3][CH3:4].Br[C:6]1[C:15]([O:16][CH3:17])=[CH:14][C:13]([N+:18]([O-:20])=[O:19])=[C:12]2[C:7]=1[CH:8]=[CH:9][CH:10]=[N:11]2.N1C=CC=CC=1>O.C([O-])(O)=O.[Na+]>[CH3:2][N:3]([CH3:4])[C:6]1[C:15]([O:16][CH3:17])=[CH:14][C:13]([N+:18]([O-:20])=[O:19])=[C:12]2[C:7]=1[CH:8]=[CH:9][CH:10]=[N:11]2A solution of 18 g (0.22 mole) of dimethylamine hydrochloride in 50 ml of warm water was added to a stirred mixture of 30 g (0.11 mole) of 5-bromo-6-methoxy-8-nitroquinoline--Example 13A--30 g of NaHCO3 and 180 ml of pyridine. The mixture was heated under reflux for 30 hr, allowed to cool and filtered. The filtered solid was washed with acetone and the combined filtrate and washings were slowly diluted with water to 4 l. Unreacted 5-bromo compound separated first followed by product. Crystallization from methanol gave 4.9 g of 5-dimethylamino-6-methoxy-8-nitroquinoline (20% yield) as orange crystals which melted 79°-80°.
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