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

HRID 245172Notes

Reaction equation

HRID 245172 reaction equation
[CH3:1][C:2]1[C:3]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)=[N:4][C:5]2[C:10]([C:11]=1[C:12]([O:14][CH3:15])=[O:13])=[CH:9][C:8](SC)=[C:7]([O:18][CH3:19])[CH:6]=2.Cl[C:31]1C=C(C=CC=1)C(OO)=O.C([O-])(O)=O.[Na+].[O-:46][S:47]([O-:50])(=S)=O.[Na+].[Na+]>ClCCl>[CH3:1][C:2]1[C:3]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)=[N:4][C:5]2[C:10]([C:11]=1[C:12]([O:14][CH3:15])=[O:13])=[CH:9][C:8]([S:47]([CH3:31])(=[O:50])=[O:46])=[C:7]([O:18][CH3:19])[CH:6]=2

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 67383617Methyl 3-methyl-7-(methyloxy)-6-(methylthio)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

Product 1

HCID 67383654Methyl 3-methyl-7-(methyloxy)-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylateYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 3-methyl-7-(methyloxy)-6-(methylthio)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (4.5 g, 8.54 mmol) and 3-chloroperoxybenzoic acid (3.85 g, 17.17 mmol) in dichloromethane (50 mL) was stirred overnight. Saturated aqueous NaHCO3 and Na2S2O3 were added slowly and the resulting mixture was stirred for 30 min. The mixture was extracted with methylene chloride (3 times). The combined organic extracts were washed with brine (2 times), 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 3-methyl-7-(methyloxy)-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (2.74 g, 71% yield). 1H NMR (400 MHz, DMSO-d6) δ8.25 (s, 1H), 7.99-8.06 (m, 2H), 7.92 (d, J=7.78 Hz, 1H), 7.82 (s, 1H), 7.76-7.82 (m, 1H), 4.11 (s, 3H), 4.09 (s, 3H), 3.41 (s, 3H), 2.38 (s, 3H); MS (m/z) 454.1 (M+H+).

Workup

  1. extractionThe mixture was extracted with methylene chloride (3 times)
  2. washThe combined organic extracts were washed with brine (2 times)
  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-c85f7134ca1a48b2ad68c59b6c35c74b
Source dataset
uspto-grants-2014_02
Patent number
US08658636B2

Reaction notes

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