m-Chloroperbenzoic acid → 4-(4-Methoxyphenyl)-2-methylpyridine 1-oxide

HRID 657661Notes

Reaction equation

HRID 657661 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([CH3:15])[CH:10]=2)=[CH:5][CH:4]=1.ClC1C=CC=C(C(OO)=[O:24])C=1>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][N+:12]([O-:24])=[C:11]([CH3:15])[CH:10]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 233717804-(4-Methoxyphenyl)-2-methylpyridine

Product 1

HCID 576720274-(4-Methoxyphenyl)-2-methylpyridine 1-oxideYield 94.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 4-(4-methoxyphenyl)-2-methylpyridine (375 mg) and metachloroperbenzoic acid (70%, 695 mg) in chloroform is stirred at room temperature for two hours. Concentration and purification over silica gel (eluent dichloromethane/methanol from 100/0 to 90/10) affords 384 mg of 4-(4-methoxyphenyl)-2-methylpyridine 1-oxide as an orange oil used without further purification.

Workup

  1. concentrationConcentration and purification over silica gel (eluent dichloromethane/methanol from 100/0 to 90/10)

Sources & evidence

ORD record
ord-855eb5495fd343ae88346529c7e01f65
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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