Methanol → 7-Fluoro-4-methoxyisoquinolin-1-OL

HRID 2361611Notes

Reaction equation

HRID 2361611 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1.CS(O)(=O)=O.[CH3:18][OH:19]>>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:19][CH3:18])=[CH:7][NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 6395Methanesulfonic AcidHCID 222501227-Fluoro-1,2-dihydroisoquinolin-1-one

Product 1

HCID 222502317-Fluoro-4-methoxyisoquinolin-1-OLYield 84%

Procedure

To a solution of 7-fluoroisoquinolin-1(2H)-one (11 g, 67.4 mmol) in methanol was added iodozobenzenediacetate (21.7 g, 67.4 mmol) followed by methane sulphonic acid (7.78 g, 81 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 and washed with water to get crude compound (11 g, 84%) as light red color solid. 1H NMR (400 MHz, CD3OD): δ ppm 8.06-8.04 (m, 1H), 7.96-7.93 (m, 1H), 7.62-7.54 (m, 2H), 6.74 (s, 1H), 3.89 (s, 3H); MS: MS m/z 194.1 (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-54c1d298cabb440aba61c8da408e04a3
Source dataset
uspto-grants-2014_04
Patent number
US08691757B2

Reaction notes

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