Hydrazine hydrate (1:1) → 6-(3-aminopropoxy)-1-methyl-1H-quinolin-2-one
Reaction equation
O.NN.[CH3:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][CH2:17][CH2:18][N:19]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]1=[O:30]>C(O)C>[NH2:19][CH2:18][CH2:17][CH2:16][O:15][C:11]1[CH:10]=[C:9]2[C:14](=[CH:13][CH:12]=1)[N:5]([CH3:4])[C:6](=[O:30])[CH:7]=[CH:8]2Participants
4
Procedure
Hydrazine hydrate (6.54 ml) was added to a ethanol solution (250 ml) of 2-[3-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)propyl]isoindole-1,3-dione (16.28 g), and stirred while heating under reflux for 2 hours. The reaction mixture was concentrated under reduced pressure. A 1N-sodium hydroxide aqueous solution was added to the residue, and stirred for 30 minutes, and extraction with dichloromethane was performed. The organic layer was washed with water and a saturated sodium chloride aqueous solution, in this order. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (8.04 g) as a colorless oil.