Methanol → 4,6-Dimethoxy-1(2H)-isoquinolinone

HRID 2361607Notes

Reaction equation

HRID 2361607 reaction equation
F[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][NH:8][C:9]2=[O:12])=[CH:4][C:3]=1[O:13][CH3:14].CS(O)(=O)=O.[CH3:20][OH:21]>>[CH3:20][O:21][C:6]1[C:5]2[C:10](=[CH:11][CH:2]=[C:3]([O:13][CH3:14])[CH:4]=2)[C:9](=[O:12])[NH:8][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 6395Methanesulfonic AcidHCID 218898267-FLUORO-6-METHOXYISOQUINOLIN-1(2H)-ONE

Product 1

HCID 222502544,6-Dimethoxy-1(2H)-isoquinolinoneYield 48.8%

Procedure

To a solution of 7-fluoro-6-methoxyisoquinolin-1(2H)-one (7 g, 40.0 mmol) in methanol (70 ml) was added iodozobenzenediacetate (14.16 g, 40.0 mmol) followed by methane sulphonic acid (11.52 g, 120 mmol) at room temperature. The reaction mass was heated at reflux for 3 h. The solvent was evaporated and the residue was diluted with cold water. The precipitated solid was filtered, washed with water to get crude compound (4 g, 48.8%) as a light red colored solid. 1H NMR (400 MHz, DMSO): δ ppm 8.11-8.09 (d, J=8 Hz, 1H), 7.19 (s, 1H), 7.13-7.11 (d, J=8 Hz, 1H), 6.72-6.71 (d, J=12 Hz, 1H), 3.89 (s, 3H), 3.79 (s, 3H); MS: MS m/z 206.1 (M++1).

Workup

  1. temperatureThe reaction mass was heated
  2. temperatureat reflux for 3 h
  3. customThe solvent was evaporated
  4. additionthe residue was diluted with cold water
  5. filtrationThe precipitated solid was filtered
  6. washwashed with water

Sources & evidence

ORD record
ord-cfeef8655c4c4e28af080d389c217def
Source dataset
uspto-grants-2014_04
Patent number
US08691757B2

Reaction notes

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