Hydrogen Peroxide → Isoquinoline, 3,4-dihydro-, 2-oxide

Participants

Reaction Conditions

Reaction Steps

A magnetic stirrer was placed in a 300-ml eggplant-type flask, followed by an addition of sodium tungstate (0.33 g, 1.0 mmol). The internal atmosphere was replaced with nitrogen. Thereafter, methanol (200 ml) and 1,2,3,4-tetrahydroisoquinoline (6.65 g, 50.0 mmol) were added successively. To the resulting mixed solution, a 30% solution of hydrogen peroxide in water (17.0 g, 150.0 mmol) was added dropwise with stirring at 0° C. in the course of 30 minutes. After stirring the mixture at room temperature for 3 hours, the solvent was driven off under reduced pressures. The residue was taken up in methylene chloride (100 ml) and then washed twice with saturated saline (30 ml). The organic phase was separated and then dried with anhydrous magnesium sulfate. The solvent was driven off under reduced pressures, thereby obtaining an yellowish oily product. The oily product was subjected to silica gel column chromatography. The column as eluted with acetone to obtain 3,4-dihydroisoquinoline-2-oxide as a nitrone (6.54 g, 89 %).

Provenance & Evidence