Triethylamine → 5-Dimethylamino-6-methoxy-8-[1-methyl-4-phthalimidobutylamino]quinoline

反応式

[NH2:1][C:2]1[CH:3]=[C:4]([O:15][CH3:16])[C:5]([N:12]([CH3:14])[CH3:13])=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.Br[CH:18]([CH3:33])[CH2:19][CH2:20][CH2:21][N:22]1[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]2[C:23]1=[O:32].C(N(CC)CC)C>CC(C)=O>[CH3:14][N:12]([CH3:13])[C:5]1[C:4]([O:15][CH3:16])=[CH:3][C:2]([NH:1][CH:18]([CH3:33])[CH2:19][CH2:20][CH2:21][N:22]2[C:26](=[O:27])[C:25]3=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]3[C:23]2=[O:32])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2

参加物

実験手順

A stirred mixture of 17.2 g (0.033 mole) of 8-amino-5-dimethylamino-6-methoxyquinoline and 9.8 g (0.033 mole) of 4-bromo-1-phthalimidopentane was maintained at 145° while 5 ml of triethylamine was added dropwise. Addition of 9.8 g of 4-bromo-1-phthalimidopentane and 5 ml of triethylamine was repeated three more times, at the same temperature (145°) at 2 hr intervals. The mixture was allowed to cool, diluted with acetone and filtered. The filtrate was concentrated to a brown oil which was diluted with ether, washed with 30% KOH and extracted with chloroform. The extract was passed through a silica column and the eluate was concentrated, dissolved in ether, treated with Darco and slowly evaporated to give yellow crystals which, after washing with petroleum ether (bp 20°-40°) weighed 9.5 g and melted at 103°-105°.