m-Chloroperbenzoic acid → HCID 18324528, compound

HRID 1251917Notes

Reaction equation

HRID 1251917 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=[C:10]([CH3:18])[N:9]=2)=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:27])C=1>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=[C:10]([CH3:18])[N+:9]=2[O-:27])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 18324447HCID 18324447, compound

Product 1

HCID 18324528HCID 18324528, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 2-(4-fluorophenyl)-6-methylpyridin-3-carboxylate (17.3 g) was dissolved in dichloromethane (600 ml), the solution cooled to 0° C. and MCPBA (24.3 g) added in portions over 25 minutes. The solution was then warmed to ambient temperature and stirred for 16 hours washed with saturated aqueous sodium bicarbonate (500 ml), dried and concentrated under reduced pressure. The residue was purified by flash column chromatography, eluting with methanol/ethyl acetate (1:12) to give 2-(4-fluorophenyl)-3-(methoxycarbonyl)-6-methylpyridine-1-oxide as a pale yellow oil which crystallised on standing (18.6 g).

Workup

  1. temperatureThe solution was then warmed to ambient temperature
  2. washwashed with saturated aqueous sodium bicarbonate (500 ml)
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography
  6. washeluting with methanol/ethyl acetate (1:12)

Sources & evidence

ORD record
ord-f6603f470944434e9aedbba0bec45f60
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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