m-Chloroperbenzoic acid → HCID 59427334, compound

HRID 1042842Notes

Reaction equation

HRID 1042842 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-8c09f21a9e0c44628820ccf8643f3351
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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