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

HRID 501442
Notes
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Reaction equation

HRID 501442 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=[Os](=O)(=O)=O.O.O1CCOCC1>[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 82029Methyl morpholine oxideHCID 230705921-Allyl-3-benzyl-4-chloro-1,3-dihydroimidazo[4,5-c]pyridin-2-oneHCID 23667635Sodium periodate

Product 1

HCID 230705823-Benzyl-4-chloro-1,3-dihydroimidazo[4,5-c]pyridin-2-oneYield 58.5%

Reagents, catalysts & solvents 3

HCID 30318Osmium Tetroxide
Catalyst
HCID 962WaterSolvent2×
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

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).

Workup

  1. extractionthe mixture was extracted with 100 ml of ethyl acetate
  2. washThe organic layer was washed twice with 50 ml of water
  3. washwashed with 50 ml of a saturated sodium chloride solution
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-db5c070109a947338be1a59eb67b9434
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07772226B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes