m-Chloroperbenzoic acid → HCID 178432335, compound

HRID 2181022Notes

Reaction equation

HRID 2181022 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:5]([N:11]=1)=[N:6][CH:7]=[CH:8][C:9]=2[CH3:10].ClC1C=CC=C(C(OO)=[O:20])C=1>C(Cl)(Cl)Cl>[CH3:1][C:2]1[NH:3][C:4]2[C:5]([N:11]=1)=[N+:6]([O-:20])[CH:7]=[CH:8][C:9]=2[CH3:10]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 223885532,7-dimethyl-1H-imidazo(4,5-b)pyridine

Product 1

HCID 178432335HCID 178432335, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2,7-dimethyl-1H-imidazo[4,5-b]pyridine (4.29 g) in chloroform (43 ml) was added m-chloroperbenzoic acid (80%, 7.55 g) at room temperature and the mixture was refluxed under heating for 1 hr. After allowing to cool to room temperature, the reaction mixture was directly purified by silica gel column chromatography (chloroform/methanol=9/1) and powdered with ethyl acetate to give 2,7-dimethyl-1H-imidazo[4,5-b]pyridine-4-oxide as a brown powder (4.61 g).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 1 hr
  3. customthe reaction mixture was directly purified by silica gel column chromatography (chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-06f7b5921c624634bcad6a7da8963014
Source dataset
uspto-grants-2005_05
Patent number
US06890934B2

Reaction notes

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