Methanol → 5-Amino-2-(pyridin-2-ylmethyl)isoquinolin-1(2H)-one
Reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[C:9]2=[O:14])([O-])=O.CO>[Pd]>[NH2:1][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[C:9]2=[O:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Into a round bottom flask was combined 5-nitro-2-(pyridin-2-ylmethyl)isoquinolin-1(2H)-one (0.7 g, 0.002 mol), palladium/C (0.05 g, 0.0005 mol) and methanol (200 mL, 5 mol). The reaction mixture was stirred under hydrogen balloon at room temperature for 40 mins. The mixture was filtered over celite, MeOH was removed and the solid was yield (0.46 mg). MS m/z=252.4 (M+1). 1H NMR (DMSO) δ 8.49 (d, J=4.3 Hz, 1H), 7.74 (td, J=7.7, 1.6 Hz, 1H), 7.42 (t, J=7.3 Hz, 2H), 7.27 (dd, J=6.9, 5.0 Hz, 1H), 7.22-7.12 (m, 2H), 6.88 (d, J=7.2 Hz, 1H), 6.80 (d, J=7.6 Hz, 1H), 5.69 (s, 2H), 5.23 (s, 2H).