N,N-Dimethylethylenediamine → 2-(2-Dimethylamino-ethyl)-5-nitro-2H-isoquinolin-1-one

HRID 1037758Notes

Reaction equation

HRID 1037758 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7]O[C:9]2=[O:14])([O-:3])=[O:2].[CH3:15][N:16]([CH3:20])[CH2:17][CH2:18][NH2:19]>CO>[CH3:15][N:16]([CH3:20])[CH2:17][CH2:18][N:19]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[CH:13][C:4]=2[N+:1]([O-:3])=[O:2])[C:9]1=[O:14]

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 100127605-nitro-1H-isochromen-1-one

Product 1

HCID 595792672-(2-Dimethylamino-ethyl)-5-nitro-2H-isoquinolin-1-oneYield 46.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Nitro-isochromen-1-one (1.0 g, 5.2 mmol) and N,N-dimethyl-1,2-ethanediamine (4 g, 40 mmol) were refluxed in methanol (40 mL) for 1.5 hours. The volatiles were removed via rotovapor and the residue was purified via flash chromatography (12 of silica gel, 0-70% EtOAc/CH2Cl2 gradient) gave 2-(2-Dimethylamino-ethyl)-5-nitro-2H-isoquinolin-1-one as a yellow solid (1.4 g, 2.4 mmol, 46%).

Workup

  1. customThe volatiles were removed via rotovapor
  2. customthe residue was purified via flash chromatography (12 of silica gel, 0-70% EtOAc/CH2Cl2 gradient)

Sources & evidence

ORD record
ord-ad5007f8d2c24f1c87404450cb50a61b
Source dataset
uspto-grants-2013_10
Patent number
US08546579B2

Reaction notes

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