7-Methoxyisoquinoline → 7-Isoquinolinol

HRID 1779959Notes

Reaction equation

HRID 1779959 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][N:9]=[CH:10]2)=[CH:5][CH:4]=1.Cl.N1C=CC=CC=1>C(OCC)(=O)C>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][N:9]=[CH:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 5943757-MethoxyisoquinolineHCID 10176127Pyridinium chloride

Product 1

HCID 4597677-IsoquinolinolYield 65.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 7.4 g of 7-methoxyisoquinoline and 30 g of pyridine hydrochloride was heated with stirring at 180° for 6 hours. The reaction mixture was allowed to cool, dissolved in ethyl acetate, and washed with a saturated aqueous sodium chloride solution. The solution was dried with anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure to give 4.43 g of 7-hydroxyisoquinoline. The compound thus obtained was dissolved in 100 ml of methylene chloride, 5.5 ml of pyridine was added and then 6.6 ml of trifluoromethanesulfonic anhydride was dropwise added. The mixture was stirred for an hour with ice cooling. After reaction, a saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture and extracted with chloroform. The chloroform layer was dried with anhydrous magnesium sulfate and the solution was concentrated under reduced pressure. The crude product thus obtained was purified by silica gel column chromatography using a mixture, ethyl acetate:n-hexane=1:3, as a developer to give 9.18 g of trifluoromethanesulfonic acid-7-isoquinolinyl.

Workup

  1. temperaturewas heated
  2. temperatureto cool
  3. washwashed with a saturated aqueous sodium chloride solution
  4. dry with materialThe solution was dried with anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5298edb8f2984d3f86de0d9b831dd158
Source dataset
uspto-grants-1997_05
Patent number
US05629321

Reaction notes

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