m-Chloroperbenzoic acid → 2-Chloro-6-methylpyridine 1-oxide

HRID 2192994Notes

Reaction equation

HRID 2192994 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.C1C=C(Cl)C=C(C(OO)=[O:17])C=1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N+:3]=1[O-:17]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 876016-Chloro-2-picoline

Product 1

HCID 45797722-Chloro-6-methylpyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2-chloro-6-methylpyridine (60.0 g, 0.47 mol) in CH2Cl2 (500 mL) was added m-CPBA (122 g, 0.700 mol), and the reaction mixture was stirred at 40° C. for 8 hours. The reaction was quenched with sodium thiosulfate and adjusted to pH=7.5 with sodium bicarbonate solution. The organic layer was washed with water, dried over sodium sulfate and the solvent was evaporated to afford 2-chloro-6-methylpyridine 1-oxide. 1H NMR (300 MHz, CDCl3) δ 7.37 (dd, J1=8.1 Hz, J2=1.5 Hz, 1H), 7.18 (dd, J1=7.8 Hz, J2=1.5 Hz, 1H), 7.07 (t, J=7.8 Hz, 1H), 2.54 (s, 3H). LRMS calc'd for (C6H6ClNO) [M+H]+, 144; found 144.

Workup

  1. customThe reaction was quenched with sodium thiosulfate
  2. washThe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-cc5d83320f034888931dd6bc9e5151b6
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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