Tetrahydrofuran → 5-Amino-2-methyl-1(2H)-isoquinolinone

Reaction equation

[CH3:1][N:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N+:12]([O-])=O)[C:3]1=[O:15].O.O.[Sn](Cl)Cl.O1CCCC1>>[NH2:12][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[CH:10]=[CH:11][N:2]([CH3:1])[C:3]2=[O:15]

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 61436Stannous chloride dihydrate

HCID 3118562-Methyl-5-nitro-2H-isoquinolin-1-one

Product 1

HCID 122203445-Amino-2-methyl-1(2H)-isoquinolinone

Procedure

2-Methyl-5-nitro-2H-isoquinolin-1-one (0.69 g, 0.0032 mol) and tin dichloride dihydrate (2 g, 0.01 mol) were stirred in tetrahydrofuran (10 mL, 0.1 mol) at room temperature overnight. The mixture was purified via flash chromatography (40 g of silica gel, 50% EtOAc/Hexanes) to give a brown solid. MS m/z (M+H) 174.9.