8-Amino-3-butyryl-4-(2-methylphenylamino)quinoline → 1-[8-(3-Morpholin-4-yl-propylamino)-4-o-tolylamino-quinolin-3-yl]-butan-1-one
Reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([C:12](=[O:16])[CH2:13][CH2:14][CH3:15])=[C:7]2[NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:24].Cl.Cl[CH2:27][CH2:28][CH2:29][N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>>[C:12]([C:8]1[CH:9]=[N:10][C:11]2[C:6]([C:7]=1[NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:24])=[CH:5][CH:4]=[CH:3][C:2]=2[NH:1][CH2:27][CH2:28][CH2:29][N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1)(=[O:16])[CH2:13][CH2:14][CH3:15]Participants
3
Procedure
8-Amino-3-butyryl-4-(2-methylphenylamino)quinoline (6.5 g, 0.02 moles) and 3-chloropropylmorpholine hydrochloride (5.0 g, 0.025 moles) were heated together in fusion (150° C) for 20 minutes. The product was partitioned between ethyl acetate and dil. ammonia solution. The organic layer was washed twice with sodium dihydrogen phosphate solution (pH5), dried, filtered and evaporated. Chromatography (silica gel/chloroform/30-0% hexane) and crystallization from hexane gave 3-butyryl-4-(2-methyl phenylamino)-8-(3-morpholinopropylamino)quinoline as orange crystals (0.45 g, 5%), m.p. 110°-11° C.