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

HRID 1037769Notes

Reaction equation

HRID 1037769 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

4

Reactant 3

HCID 8028TetrahydrofuranHCID 61436Stannous chloride dihydrateHCID 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.

Workup

  1. customThe mixture was purified via flash chromatography (40 g of silica gel, 50% EtOAc/Hexanes)
  2. customto give a brown solid

Sources & evidence

ORD record
ord-1c7aaa3657c348daa9a1bd6a19ae6e99
Source dataset
uspto-grants-2013_10
Patent number
US08546579B2

Reaction notes

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