m-Chloroperbenzoic acid → 2-(2-Methoxy-4-trifluoromethoxy-phenyl)-3-methyl-5-nitro-pyridine 1-oxide

HRID 2179997Notes

Reaction equation

HRID 2179997 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH3:12][O:13][C:14]1[CH:19]=[C:18]([O:20][C:21]([F:24])([F:23])[F:22])[CH:17]=[CH:16][C:15]=1[C:25]1[C:30]([CH3:31])=[CH:29][C:28]([N+:32]([O-:34])=[O:33])=[CH:27][N:26]=1>C(Cl)Cl>[CH3:12][O:13][C:14]1[CH:19]=[C:18]([O:20][C:21]([F:24])([F:22])[F:23])[CH:17]=[CH:16][C:15]=1[C:25]1[C:30]([CH3:31])=[CH:29][C:28]([N+:32]([O-:34])=[O:33])=[CH:27][N+:26]=1[O-:9]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 224900532-(2-Methoxy-4-trifluoromethoxy-phenyl)-3-methyl-5-nitro-pyridine

Product 1

HCID 224900552-(2-Methoxy-4-trifluoromethoxy-phenyl)-3-methyl-5-nitro-pyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

MCPBA (78.26 g, 0.349 mol) is added to a solution of 2-(2-methoxy-4-trifluoromethoxy-phenyl)-3-methyl-5-nitro-pyridine (95.6 g, 0.291 mol) in CH2Cl2 (500 ml) at room temperature. The mixture is stirred at room temperature for 3 hours. (1.2 L) and hexane (300 ml) and the mixture is washed with saturated aqueous Na2CO3 and brine. After drying over Na2SO4, the solvent is removed under reduced pressure to give 2-(2methoxy-4-trifluoromethoxy-phenyl)-3-methyl-5-nitro-pyridine 1-oxide as yellow solid. Rf (hexane/EtOAc=1:1)=0.40.

Workup

  1. wash(1.2 L) and hexane (300 ml) and the mixture is washed with saturated aqueous Na2CO3 and brine
  2. dry with materialAfter drying over Na2SO4
  3. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-2533471316b74b5dbddfa835556694f0
Source dataset
uspto-grants-2005_05
Patent number
US06887875B2

Reaction notes

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