7-Amino-2-methyl-1,2,3,4-tetrahydroquinoline → 2-Methylquinolin-7-amine
Reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH3:12])[NH:9]2)=[CH:4][CH:3]=1>C1(C)C(C)=CC=CC=1.[Pd]>[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH3:12])=[N:9]2)=[CH:4][CH:3]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 7-amino-2-methyl-1,2,3,4-tetrahydroquinoline (D65) (86 mg) and wet 10% palladium/charcoal (25 mg) in xylene (20 ml) was heated at reflux for 3.5 h. After cooling to room temperature the catalyst was removed via filtration and washed with further xylene. Evaporation of the combined filtrate and washings gave the title compound as a crude off-white solid (87 mg) which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ (ppm): 7.87 (d, 1H), 7.56 (d, 1H), 7.14 (d, 1H), 7.03 (d, 1H), 6.91 (dd, 1H), 4.02 (br, 2H), 2.67 (s, 3H).