tert-Butyl 2-methyl-6-nitro-4-phenylquinoline-3-carboxylate → tert-Butyl 6-amino-2-methyl-4-phenylquinoline-3-carboxylate
Reaction equation
[CH3:1][C:2]1[C:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[C:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:25]([O-])=O)[CH:8]=2)[N:3]=1>CCOC(C)=O.[Pd]>[NH2:25][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([CH3:1])[C:11]([C:12]([O:14][C:15]([CH3:18])([CH3:16])[CH3:17])=[O:13])=[C:10]2[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1Participants
4
Procedure
A mixture of the product of Step 1 (1.05 g, 3.25 mmol) and 10% Pd/C (0.222 g, 32.5) in EtOAc was degassed under reduced pressure and saturated with H2 gas. The resulting mixture was stirred overnight under H2 balloon at room temperature, filtered through Celite bed and filtrate evaporated to dryness to give product as an yellowish solid (1.46 g, 98%), which was used in next step without further purification. 1H NMR (300 MHz, CDCl3) δ 7.83 (d, J=8.9 Hz, 1H), 7.43-7.48(m, 3H), 7.27-7.34(m, 2H), 7.10 (dd, J=2.5, 8.9 Hz, 1H), 6.55(d, J=2.5 Hz, 1H), 3.79(broad s, 2H), 2.69(s, 3H), 1.2(s, 9H).