m-Chloroperbenzoic acid → 5-Fluoro-2,3-dimethyl-1-oxidopyridin-1-ium

HRID 1592428Notes

Reaction equation

HRID 1592428 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]([CH3:9])=[C:6]([CH3:8])[CH:7]=1.ClC1C=C(C=CC=1)C(OO)=[O:15]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[N+:4]([O-:15])[C:5]([CH3:9])=[C:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 450799815-Fluoro-2,3-dimethylpyridine

Product 1

HCID 197912325-Fluoro-2,3-dimethyl-1-oxidopyridin-1-ium

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-fluoro-5,6-dimethyl-pyridine (0.230 g, 1.84 mmol) (Ife, R. J. Eur. Pat. Appl. (1987), EP 246774), 3-chloroperoxybenzoic acid (77%, 1.24 g, 5.5 mmol) in CH2Cl2 (25 mL) was stirred for 16 h. The solution was concentrated, and the residue was purified by flash chromatography on a silica gel column (8:1 EtOAc/MeOH), affording 3-fluoro-5,6-dimethyl-pyridine-1-oxide as a white solid (0.225 g 87%).

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue was purified by flash chromatography on a silica gel column (8:1 EtOAc/MeOH)

Sources & evidence

ORD record
ord-26725b8ee86f4a00b05015fc9d56a312
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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