7-Amino-4,4-dimethyl-3,4-dihydroquinolin-2(1H)-one → 4,4-Dimethyl-1,2,3,4-tetrahydroquinolin-7-amine
Reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:14])([CH3:13])[CH2:7][C:8](=O)[NH:9]2)=[CH:4][CH:3]=1>C1COCC1>[CH3:13][C:6]1([CH3:14])[C:5]2[C:10](=[CH:11][C:2]([NH2:1])=[CH:3][CH:4]=2)[NH:9][CH2:8][CH2:7]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
The mixture of 7-amino-4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one (1.07 g, 5.62 mmol) and borane dimethylsulfide complex (1.60 ml, 16.9 mmol) in 40 ml of anhydrous THF was heated at reflux under N2 for 15 h. The solvents were removed under reduced pressure. The residue was heated at reflux in 20 ml of MeOH for 2 h, then 0.80 g of NaHCO3 was added, and the mixture was heated at reflux for 2 h. The mixture was filtered, condensed, and the residue was purified by flash column chromatography (5 to 10% of EtOAc in CH2Cl2). The titled compound was obtained as a viscous oil. MS (ES+): 176.9 (M+H)+. Calc'd for C11H16N—176.26.