m-Chloroperbenzoic acid → 5-(2-Fluoro-4-methylphenyl)nicotinic acid 1-oxide

HRID 1909149Notes

Reaction equation

HRID 1909149 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[N:11][CH:12]=[C:13]([CH:17]=1)[C:14]([OH:16])=[O:15].ClC1C=CC=C(C(OO)=[O:26])C=1>ClCCl.CO>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[N+:11]([O-:26])[CH:12]=[C:13]([CH:17]=1)[C:14]([OH:16])=[O:15]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acid3×HCID 532228005-(2-Fluoro-4-methylphenyl)nicotinic acid

Product 1

HCID 673383365-(2-Fluoro-4-methylphenyl)nicotinic acid 1-oxideYield 65.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(2-fluoro-4-methylphenyl)nicotinic acid (0.15 g, 0.43 mmol) in dichloromethane (5 mL) and methanol (3 mL) was added 3-chloroperbenzoic acid (70%; 0.16 g, 0.65 mmol). The mixture was stirred at ambient temperature. After 18 h, additional 3-chloroperbenzoic acid (70%; 0.19 g, 0.86 mmol) was added. The mixture was continued to stir at ambient temperature. After 24 h, additional 3-chloroperbenzoic acid (70%; 0.19 g, 0.86 mmol) was added. After 18 h, the mixture was concentrated. Purification by reverse chromatography (C-18, 95% water/acetonitrile→25% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (70 mg). MS 248.0 (M+1).

Workup

  1. stirringto stir at ambient temperature
  2. waitAfter 24 h
  3. waitAfter 18 h
  4. concentrationthe mixture was concentrated
  5. customPurification by reverse chromatography (C-18, 95% water/acetonitrile→25% water/acetonitrile with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-0e13f5d8e963455486bf69be6b541367
Source dataset
uspto-grants-2013_12
Patent number
US08598209B2

Reaction notes

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