m-Chloroperbenzoic acid → 6-benzoyl-2-methylpyridine N-oxide

HRID 27708Notes

Reaction equation

HRID 27708 reaction equation
[C:1]([C:9]1[N:14]=[C:13]([CH3:15])[CH:12]=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:24])C=1>C(Cl)(Cl)Cl>[C:1]([C:9]1[N+:14]([O-:24])=[C:13]([CH3:15])[CH:12]=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 126232682-Benzoyl-6-methylpyridine

Product 1

HCID 545239806-benzoyl-2-methylpyridine N-oxide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

The 6-benzoyl-2-methylpyridine (3.9 g, 21 mmol), in 20 ml CHCl3, is added over 1 hour to 4.2 g (21 mmol) m-chloroperbenzoic acid (in 50 ml CHCl3). The temperature is kept below 25° as the mixture is stirred overnight. The reaction is diluted with CHCl3, washed with sat. NaHSO3, water, 20% NaHCO3 (2×) and then water, dried, stripped and finally titrated with hexane/ethyl acetate to give 6-benzoyl-2-methylpyridine N-oxide.

Workup

  1. customis kept below 25° as the mixture
  2. washwashed with sat. NaHSO3, water, 20% NaHCO3 (2×)
  3. dry with materialwater, dried

Sources & evidence

ORD record
ord-0104fad4fc1642d0ba6fc267050a9c06
Source dataset
uspto-grants-1980_09
Patent number
US04223033

Reaction notes

Loading…