Methanesulfonic Acid → HCID 68500303, compound

HRID 888409Notes

Reaction equation

HRID 888409 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:14]=[C:15]([C:17]([CH3:19])=[CH2:18])[CH:16]=2)[C:11]([OH:13])=[O:12])=[N:6][CH:7]=1.CS(O)(=O)=[O:22].C(=O)([O-])[O-].[Na+].[Na+]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:14]=[C:15]([C:17]([OH:22])([CH3:19])[CH3:18])[CH:16]=2)[C:11]([OH:13])=[O:12])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 10340Sodium CarbonateHCID 685013473-(5-Chloropyridin-2-yl)-5-isopropenylbenzoic acid

Product 1

HCID 68500303HCID 68500303, compoundYield 59.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-(5-chloropyridin-2-yl)-5-isopropenylbenzoic acid (0.18 g, 0.46 mmol) in water (4.6 mL) was added methanesulfonic acid (1.5 mL, 23.1 mmol). The mixture was heated to 50° C. After 18 h, the mixture was cooled to ambient temperature and sodium carbonate was added to adjust pH to 3-4. The mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by reverse phase chromatography (C-18, 100% water/acetonitrile→25% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (80 mg). MS 292.1 (M+1).

Workup

  1. temperaturethe mixture was cooled to ambient temperature
  2. extractionThe mixture was extracted with ethyl acetate (3×)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by reverse phase chromatography (C-18, 100% water/acetonitrile→25% water/acetonitrile with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-cb8516dd905d4793b9632f92113854b6
Source dataset
uspto-grants-2012_08
Patent number
US08247401B2

Reaction notes

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