Hydrochloric Acid → HCID 57667943, compound

HRID 2191670Notes

Reaction equation

HRID 2191670 reaction equation
[Mn]([O-])(=O)(=O)=O.[K+].N1C=CC=CC=1.[C:13]([C:21]1[CH:22]=[CH:23]C(C)=[C:25]([N:27]([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[C:28](=[O:30])[CH3:29])[CH:26]=1)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl.[C:40]([O:43]CC)(=[O:42])[CH3:41]>O>[C:13]([C:21]1[CH:22]=[CH:23][C:41]([C:40]([OH:43])=[O:42])=[C:25]([N:27]([C:31]2[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=2)[C:28](=[O:30])[CH3:29])[CH:26]=1)(=[O:20])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 8857Ethyl AcetateHCID 516875Potassium Permanganate4×HCID 57668003HCID 57668003, compound

Product 1

HCID 57667943HCID 57667943, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Potassium permanganate 0.24 g was added to a mixed solution of pyridine 5.0 mL and water 5.0 mL of N-(5-benzoyl-2-methylphenyl)-N-(4-fluorophenyl)acetamide 0.52 g at room temperature, and it was heated and refluxed for 30 minutes. After the reaction mixture was cooled to room temperature, potassium permanganate 0.24 g was added to it, it was heated and refluxed for 30 minutes. After the reaction mixture was cooled to room temperature, potassium permanganate 0.24 g was added to it, it was heated and refluxed for 30 minutes. After the reaction mixture was cooled to room temperature, furthermore, potassium permanganate 0.24 g was added to it, and it was heated and refluxed for 30 minutes. After the reaction mixture was cooled, ethyl acetate was added to it, it was adjusted to pH2.3 with 6.0 mol/L hydrochloric acid, and insoluble matter was filtrated. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after sequential washing with 1.0 mol/L hydrochloric acid and saturated sodium chloride aqueous solution, the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [eluent; hexane:ethyl acetate=1:2] to give 4-benzoyl-2-(N-(4-fluorophenyl)acetamido)benzoic acid 0.39 g of white solid.

Workup

  1. temperatureit was heated
  2. temperaturerefluxed for 30 minutes
  3. temperaturewas heated
  4. temperaturerefluxed for 30 minutes
  5. temperatureAfter the reaction mixture was cooled to room temperature
  6. temperaturewas heated
  7. temperaturerefluxed for 30 minutes
  8. temperatureAfter the reaction mixture was cooled to room temperature
  9. temperaturewas heated
  10. temperaturerefluxed for 30 minutes
  11. temperatureAfter the reaction mixture was cooled
  12. filtrationwas filtrated
  13. customThe organic layer was separated
  14. washafter sequential washing with 1.0 mol/L hydrochloric acid and saturated sodium chloride aqueous solution
  15. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-cd86596137074e47a8771d0342fbc77a
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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