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

HRID 2112913Notes

Reaction equation

C[N+]1([O-])CCOCC1.I([O-])(=O)(=O)=O.[Na+].C([N:18]1[C:26]2[CH:25]=[CH:24][N:23]=[C:22]([Cl:27])[C:21]=2[N:20]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:19]1=[O:35])C=C>O.O1CCOCC1.O=[Os](=O)(=O)=O>[CH2:28]([N:20]1[C:21]2[C:22]([Cl:27])=[N:23][CH:24]=[CH:25][C:26]=2[NH:18][C:19]1=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Water (1.5 mL), 4-methylmorpholin-N-oxide (1.06 g), 2% aqueous osmic acid solution (3 mL), and a solution of sodium periodate (1.94 g) in water (6 mL) were added to a solution of 1-allyl-3-benzyl-4-chloro-1,3-dihydroimidazo[4.5-c]pyridin-2-one (0.75 g) in 1,4-dioxane (15 mL). This was then heated at 60° C. for 18 hours. Water (200 mL) was added, and this was extracted with ethyl acetate (100 mL). The obtained organic layer was washed twice with 50 mL of water and then once with 50 mL of saturated aqueous sodium chloride solution, dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography, and the fraction eluted by ethyl acetate-hexane (1:1) gave the title compound (0.38 g).

Workup

extractionthis was extracted with ethyl acetate (100 mL)
washThe obtained organic layer was washed twice with 50 mL of water
dry with materialonce with 50 mL of saturated aqueous sodium chloride solution, dried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography
washthe fraction eluted by ethyl acetate-hexane (1:1)

Sources & evidence

ORD record: ord-7b999b6c467b4c469708e750c35aa4c3
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07524847B2

Reaction notes

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