Methanol → (R)-2-(5-Amino-1-oxoisoquinolin-2(1H)-yl)-2-phenylacetamide
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]([C@H:15]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:16]([NH2:18])=[O:17])[C:9]2=[O:14])([O-])=O.CO>>[NH2:1][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]([C@H:15]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:16]([NH2:18])=[O:17])[C:9]2=[O:14]Participants
3
Procedure
A round bottom flask was charged with (R)-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)-2-phenylacetamide (2.3 g, 0.0071 mol), methanol (30 mL, 0.7 mol) palladium, 10% weight on charcoal (110 mg, 0.00090 mol) was added and the flask was evacuated of air and stirred under hydrogen atmosphere (1 atm) for 1.5 h. The reaction mixture was filtered over celite and the solvent removed under pressure. The residue was purified by flash chromatography (40 g silica, 0-10% MeOH/DCM) to obtain the product as a light yellow solid. MS m/z=294.5 (M+H).
Workup
- additionwas added
- customthe flask was evacuated of air