m-Chloroperbenzoic acid → HCID 59427334, compound

HRID 2359698Notes

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([O-])(O)=O.[Na+]>ClCCl>[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

Conditions

Temperature: -78 °C

Procedure

In a 50 mL round bottom flask under N2, was dissolved 7-methoxy-4-(phenylthio)quinoline (1.38 g, 5.16 mmol) in 50 mL of dichloromethane then cooled to −78° C. Solid m-CPBA (77%) (1.25 g, 7.23 mmol) was added portionwise to the reaction, and the mixture was warmed slowly over 3 h to rt. After 3 h, the reaction mixture was diluted with dichloromethane and then neutralized with aqueous NaHCO3 (sat). The aqueous phase was extracted three times with dichloromethane, and then the organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude mixture was purified by MPLC (ISCO. DCM:MeOH 100:0 to 90:10) to afford 7-methoxy-4-(phenylsulfinyl)quinoline (1.37 g, 93.7% yield) as an off-white foam. MS (ESI pos. ion) m/z: 284 (MH+). Calc'd exact mass for C16H13NO2S: 283.

Workup

temperaturethe mixture was warmed slowly over 3 h to rt
extractionThe aqueous phase was extracted three times with dichloromethane
dry with materialthe organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude mixture was purified by MPLC (ISCO. DCM:MeOH 100:0 to 90:10)

Sources & evidence

ORD record: ord-d7f7190015dc46d98baf19c9312759fe
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08685983B2

Reaction notes

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