m-Chloroperbenzoic acid → 4-Trifluoromethyl-2-picoline-N-oxide

HRID 2103404Notes

Reaction equation

HRID 2103404 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=1.ClC1C=CC=C(C(OO)=[O:20])C=1>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:11])[F:10])[CH:5]=[CH:4][N+:3]=1[O-:20]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 147614442-Methyl-4-(trifluoromethyl)pyridine

Product 1

HCID 147614494-Trifluoromethyl-2-picoline-N-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-4-(trifluoromethyl)pyridine (3.9 g, 24 mmol) in methylene chloride (50 mL) was added m-chloroperbenzoic acid (7.0 g, 31 mmol). After being stirred at room temperature overnight, the solution was washed with 50 mL of 1 N NaOH. The water phase was back-extracted with methylene chloride. The combined organic phases were dried over Na2SO4 and concentrated under vacuum to give the title compound. MS (M+H) 178.1.

Workup

  1. washthe solution was washed with 50 mL of 1 N NaOH
  2. extractionThe water phase was back-extracted with methylene chloride
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-017604c2ca07434f86a150d1e967a373
Source dataset
uspto-grants-2009_08
Patent number
US07576089B2

Reaction notes

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