Sodium Thiosulfate → Methyl 6-(ethylsulfonyl)-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

HRID 245161Notes

Reaction equation

HRID 245161 reaction equation
C(S[C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]=[C:9]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=1)[C:8]([CH3:26])=[C:7]2[C:27]([O:29][CH3:30])=[O:28])C.Cl[C:32]1C=C(C=C[CH:41]=1)C(OO)=O.C([O-])(O)=O.[Na+].[O-:47][S:48]([O-:51])(=S)=O.[Na+].[Na+]>ClCCl>[CH2:32]([S:48]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]=[C:9]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:23])([F:24])[F:25])[CH:17]=1)[C:8]([CH3:26])=[C:7]2[C:27]([O:29][CH3:30])=[O:28])(=[O:51])=[O:47])[CH3:41]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 67418873Methyl 6-(ethylthio)-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

Product 1

HCID 67384351Methyl 6-(ethylsulfonyl)-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylateYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 6-(ethylthio)-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (7.05 g, 11.33 mmol) and 3-chloroperoxybenzoic acid (5.11 g, 22.7 8 mmol) in dichloromethane (50 mL) was stirred overnight. Saturated aqueous NaHCO3 and Na2S2O3 were added slowly, and the mixture was stirred for 30 min and extracted three times with methylene chloride. The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified via column chromatography (ISCO, 0-15% ethyl acetate/methylene chloride) to give methyl 6-(ethylsulfonyl)-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (3.4 g, 64% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.24 (s, 1H), 7.98-8.05 (m, 2H), 7.92 (d, J=8.03 Hz, 1H), 7.76-7.85 (m, 2H), 4.10 (s, 3H), 4.09 (s, 3H), 3.54 (q, J=7.53 Hz, 2H), 2.37 (s, 3H), 1.15 (t, J=7.40 Hz, 3H); MS (m/z) 468.1 (M+H+).

Workup

  1. extractionextracted three times with methylene chloride
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified via column chromatography (ISCO, 0-15% ethyl acetate/methylene chloride)

Sources & evidence

ORD record
ord-3142e3c840224edf80a1aac044cf5404
Source dataset
uspto-grants-2014_02
Patent number
US08658636B2

Reaction notes

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