m-Chloroperbenzoic acid → HCID 59427334, compound

HRID 503577Notes

Reaction equation

HRID 503577 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([S:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.C1C=C(Cl)C=C(C(OO)=[O:28])C=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([S:13]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:28])=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59598389HCID 59598389, compound

Product 1

HCID 59427334HCID 59427334, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 7-methoxy-4-(phenylthio)quinoline (1.38 g, 5.16 mmol) in CH2Cl2(50 mL) at −78° C. was added m-CPBA (77%)(1.25 g, 7.23 mmol) and the mixture was allowed to slowly warm to RT (ca. 1 h). The mixture was diluted with CH2Cl2 and washed with saturated NaHCO3. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude mixture was purified by silica gel chromatography using CH2Cl2:MeOH 100:0 to 90:10 to afford 7-methoxy-4-(phenylsulfinyl)quinoline as a off-white solid. MS found: M+H+=284.0.

Workup

  1. washwashed with saturated NaHCO3
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0339b5bcd39548d29e79f4ac69219351
Source dataset
uspto-grants-2010_08
Patent number
US07776857B2

Reaction notes

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