Methanol → 2-Methyl-5-nitro-2H-isoquinolin-1-one

HRID 1037768Notes

Reaction equation

HRID 1037768 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][O:8][C:9]2=O)([O-:3])=[O:2].[CH3:15][NH2:16].CO>>[CH3:15][N:16]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:8]

Participants

4

Reactant 3

HCID 887MethanolHCID 6329MethylamineHCID 100127605-nitro-1H-isochromen-1-one

Product 1

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

Procedure

5-Nitro-isochromen-1-one (1.2 g, 0.0063 mol) and 40% aqueous methylamine (10 mL, 0.09 mol) were refluxed in methanol (40 mL, 1 mol) for 1 hour. The solvents were removed and the residue was diluted with CH2Cl2/MeOH (95:5 v/v, 100 mL), washed with brine (20 mL×2). The CH2Cl2 layer was dried over Na2SO4, purified via flash chromatography (40 g of silica gel, 0-50% EtOAc/Hexanes) to give a yellow solid. MS m/z (M+H) 204.8.

Workup

  1. customThe solvents were removed
  2. additionthe residue was diluted with CH2Cl2/MeOH (95:5 v/v, 100 mL)
  3. washwashed with brine (20 mL×2)
  4. dry with materialThe CH2Cl2 layer was dried over Na2SO4
  5. custompurified via flash chromatography (40 g of silica gel, 0-50% EtOAc/Hexanes)
  6. customto give a yellow solid

Sources & evidence

ORD record
ord-a7dd85779aca47559ff4afc662d6d59b
Source dataset
uspto-grants-2013_10
Patent number
US08546579B2

Reaction notes

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