m-Chloroperbenzoic acid → 2-(4-methylphenyl)-6-methylpyridine-N-oxide

HRID 22257

Reaction equation

HRID 22257 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[N:9]=2)=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:23])C=1>C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[N+:9]=2[O-:23])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 6030812-Methyl-6-(4-methylphenyl)pyridine

Product 1

HCID 194303302-(4-methylphenyl)-6-methylpyridine-N-oxideYield 57.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 2-(4-methylphenyl)-6-methylpyridine (4.5 g) in 100 ml of chloroform was cooled to 0° C., and m-chloroperbenzoic acid (7.7 g) in 50 ml of chloroform was added over a period of 15 minutes. The mixture was stirred at room temperature for 3 hours, then at 50° C. for 2 hours, followed by stirring overnight at room temperature. Solvent was evaporated to a small volume under reduced pressure, and the residue passed through an alumina column, eluting with 2% methanol in methylene chloride to remove benzoic acid. The eluate was flash-Chromatographed on silica gel, eluting with 5% methanol in methylene chloride, to yield 2.8 g of 2-(4-methylphenyl)-6-methylpyridine-N-oxide, m.p. 95° C.

Workup

  1. waitat 50° C. for 2 hours
  2. stirringby stirring overnight at room temperature
  3. customSolvent was evaporated to a small volume under reduced pressure
  4. washeluting with 2% methanol in methylene chloride
  5. customto remove benzoic acid
  6. washeluting with 5% methanol in methylene chloride

Sources & evidence

ORD record
ord-c5f37f607fa446e491d9d67022356215
Source dataset
uspto-grants-1995_06
Patent number
US05428037

Linked notes

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