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

HRID 1037762Notes

Reaction equation

HRID 1037762 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 3

HCID 887MethanolHCID 66053N,N-DimethylethylenediamineHCID 100127605-nitro-1H-isochromen-1-one

Product 1

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

Procedure

5-Nitro-isochromen-1-one (1.83 g, 0.00957 mol) and N,N-dimethyl-1,2-ethanediamine (3 g, 0.03 mol) were refluxed in methanol (20 mL, 0.5 mol) for 1 hour. The volatiles were removed via rotovapor. The residue was purified via flash chromatography (40 g of silica gel, 50% EtOAc/CH2Cl2) and gave a light yellow solid.

Workup

  1. customThe volatiles were removed via rotovapor
  2. customThe residue was purified via flash chromatography (40 g of silica gel, 50% EtOAc/CH2Cl2)
  3. customgave a light yellow solid

Sources & evidence

ORD record
ord-d87f8241621344a084dc7e07d8405513
Source dataset
uspto-grants-2013_10
Patent number
US08546579B2

Reaction notes

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