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

HRID 245154Notes

Reaction equation

HRID 245154 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+].[S:44]([O-:48])([O-])(=O)=[O:45].[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:44]([CH3:29])(=[O:48])=[O:45])=[CH:7][CH:6]=2

Participants

6

Reactant 4

HCID 24436Sodium SulfateHCID 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 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 3-methyl-6-(methylthio)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (1.5 g, 3.83 mmol) and 3-chloroperoxybenzoic acid (1.46 g, 8.43 mmol) in dichloromethane (50 mL) was stirred overnight. Saturated aqueous sodium bicarbonate and sodium sulfate were added and the mixture was stirred for 30 min. The aqueous mixture was extracted with methylene chloride (3 times). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified via column chromatography (ISCO, 10-40% ethyl acetate/hexanes) to afford methyl 3-methyl-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (1.22 g, 75% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.31-8.39 (m, 2H), 8.26-8.31 (m, 1H), 8.00-8.08 (m, 2H), 7.93 (d, J=7.78 Hz, 1H), 7.80 (t, J=7.65 Hz, 1H), 4.12 (s, 3H), 3.40 (s, 3H), 2.42 (s, 3H); MS (m/z) 424.0 (M+H+).

Workup

  1. extractionThe aqueous mixture was extracted with methylene chloride (3 times)
  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, 10-40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-eca0de56805e4905b064e588ca7eec99
Source dataset
uspto-grants-2014_02
Patent number
US08658636B2

Reaction notes

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