2-(2-Dimethylamino-ethyl)-5-nitro-2H-isoquinolin-1-one → 5-Amino-2-(2-dimethylamino-ethyl)-2H-isoquinolin-1-one

HRID 1037763Notes

Reaction equation

HRID 1037763 reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][N:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[N+:15]([O-])=O)[C:6]1=[O:18]>CO.[Pd]>[NH2:15][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[CH:13]=[CH:14][N:5]([CH2:4][CH2:3][N:2]([CH3:19])[CH3:1])[C:6]2=[O:18]

Participants

4

Reactant 1

HCID 595792672-(2-Dimethylamino-ethyl)-5-nitro-2H-isoquinolin-1-one

Product 1

HCID 595794535-Amino-2-(2-dimethylamino-ethyl)-2H-isoquinolin-1-oneYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-(2-Dimethylamino-ethyl)-5-nitro-2H-isoquinolin-1-one (1.10 g, 0.00358 mol) was dissolved in MeOH (30 mL), Pd/C (10%) was added and the mixture was stirred under an atmosphere of hydrogen at room temperature for 1 h. The mixture was filtered through Celite, and the solvent was removed in vacuo to give the titled product as a light yellow solid (0.82 g). MS m/z (M+H) 232.4.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a4ad5c008c58474798cf351f53e61f03
Source dataset
uspto-grants-2013_10
Patent number
US08546579B2

Reaction notes

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