Sodium Thiosulfate → Methyl 3-methyl-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

HRID 245232Notes

Reaction equation

HRID 245232 reaction equation
[CH3:1][C:2]1[C:3]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)=[N:4][C:5]2[C:10]([C:11]=1[C:12]([O:14][CH3:15])=[O:13])=[CH:9][C:8](SC)=[CH:7][CH:6]=2.Cl[C:29]1C=C(C=CC=1)C(OO)=O.C([O-])(O)=O.[Na+].[O-:44][S:45]([O-:48])(=S)=O.[Na+].[Na+]>ClCCl>[CH3:1][C:2]1[C:3]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)=[N:4][C:5]2[C:10]([C:11]=1[C:12]([O:14][CH3:15])=[O:13])=[CH:9][C:8]([S:45]([CH3:29])(=[O:48])=[O:44])=[CH:7][CH:6]=2

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 67417678Methyl 3-methyl-6-(methylthio)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

Product 1

HCID 67383507Methyl 3-methyl-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 3-methyl-6-(methylthio)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (2.45 g, 6.26 mmol) and 3-chloroperoxybenzoic acid (2.376 g, 13.77 mmol) in dichloromethane (50 mL) was stirred overnight. Saturated aqueous NaHCO3 and Na2S2O3 were added slowly, and the mixture was stirred for 30 min. The mixture was extracted with methylene chloride (three times). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was purified via column chromatography (ISCO, 10-60% ethyl acetate/hexanes) to give methyl 3-methyl-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (2.59 g, 98% yield). MS (m/z) 424.1 (M+H+).

Workup

  1. extractionThe mixture was extracted with methylene chloride (three times)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified via column chromatography (ISCO, 10-60% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-2e224a975d174e8eb440aee908a6fe8d
Source dataset
uspto-grants-2014_02
Patent number
US08658636B2

Reaction notes

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