Methyl morpholine oxide → 3-Benzyl-4-chloro-1,3-dihydroimidazo[4,5-c]pyridin-2-one

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Reaction Conditions

Reaction Steps

1.5 ml of water, 1.06 g of 4-methyl morpholine N-oxide, 3 ml of an aqueous solution of 2% osmic acid, and a 6 ml aqueous solution of 1.94 g of sodium periodate were added to a 15 ml 1,4-dioxane solution of 0.75 g of 1-allyl-3-benzyl-4-chloro-1,3-dihydroimidazo[4,5-c]pyridin-2-one, and the mixture was heated at 60° C. for 18 hours. 200 ml of water was added to the solution, and the mixture was extracted with 100 ml of ethyl acetate. The organic layer was washed twice with 50 ml of water and then washed with 50 ml of a saturated sodium chloride solution. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography. Thus, 0.38 g of the title compound was obtained from the fraction eluted with ethyl acetate-hexane (1:1).

Provenance & Evidence