Sodium periodate → 1-oxo-1,2,3,4-tetrahydroisoquinoline-7-carbaldehyde

Participants

Reaction Steps

To a solution of 7-ethenyl-3,4-dihydro-1(2H)-isoquinolinone (232 mg, 1.341 mmol) in 1,4-dioxane (15 ml) and water (3 ml) at 0° C. was added sodium periodate (660 mg, 3.08 mmol) and osmium tetroxide (1.5 ml of a 4% aqueous solution). The reaction mixture was warmed to room temperature and stirred for 0.5 h before evaporation of the reaction mixture. The residue was dissolved in 1,4-dioxane (50 ml) and evaporated again. The mixture was then dissolved in dichloromethane (100 ml), dried with magnesium sulphate and evaporated. Chromatography on silica, eluting with 0-100% ethyl acetate/hexane, gave the product (133 mg, 57%).

Provenance & Evidence