m-Chloroperbenzoic acid → HCID 13373741, compound

HRID 485082Notes

Reaction equation

HRID 485082 reaction equation
[F:1][C:2]1[C:11]([F:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:13])=[N:7]2.ClC1C=CC=C(C(OO)=[O:22])C=1>C(Cl)(Cl)Cl>[F:1][C:2]1[C:11]([F:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:13])=[N+:7]2[O-:22]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 13373740HCID 13373740, compound

Product 1

HCID 13373741HCID 13373741, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

1.0 g of 5,6-difluoro-2-methylquinoline was dissolved in 30 ml of chloroform and then a mixture of 20 ml of chloroform and 1.0 g of 3-chloroperbenzoic acid was added dropwise thereto under cooling in an ice bath. The resulting mixture was stirred for 2 hours at 0° C. and for additional one hour at room temperature. The reaction mixture was washed twice with a saturated aqueous solution of sodium bicarbonate and washed with a saturated aqueous solution of sodium chloride. After drying, the solvent was distilled off in vacuo and the residue was purified by silica gel column chromatography to give 830 mg of 5,6-difluoro-2-methylquinoline-1-oxide. The product was recrystallized from a mixture of benzene and hexane to give a white powder with mp 125°-127° C.

Workup

  1. additionwas added dropwise
  2. temperatureunder cooling in an ice bath
  3. washThe reaction mixture was washed twice with a saturated aqueous solution of sodium bicarbonate
  4. washwashed with a saturated aqueous solution of sodium chloride
  5. customAfter drying
  6. distillationthe solvent was distilled off in vacuo
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5246bcbcbf8c44e49ae1108220f2846a
Source dataset
uspto-grants-1985_08
Patent number
US04535161

Reaction notes

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