Methyl iodide → 5-Methoxyisoquinoline

HRID 2416566Notes

Reaction equation

HRID 2416566 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.CI.[C:14](=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C>[CH3:14][O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 30386Isoquinolin-5-ol

Product 1

HCID 137542835-Methoxyisoquinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.6 g (38.6 mmol) of 5-hydroxyisoquinoline was dissolved in 70 ml of DMF. 2.63 ml (38.6 mmol) of methyl iodide and 7.99 g (57.9 mmol) of potassium carbonate were added to the obtained solution, and they were stirred at room temperature overnight. After the treatment with ethyl acetate as the extracting solvent in an ordinary manner, the crude product was obtained. It was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. customIt was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-9f1de59196f64f03b6a611dd8a8de81f
Source dataset
uspto-grants-2004_11
Patent number
US06825181B1

Reaction notes

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