Acetic Acid → Indoprofen

HRID 1660451Notes

Reaction equation

HRID 1660451 reaction equation
C(O)(=O)C.CS[C:7]([C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]2=[O:27])=[CH:14][CH:13]=1)([CH3:11])[C:8]([OH:10])=[O:9].Cl.O>S([O-])([O-])(=O)=O.[Cu+2].[Zn].C(Cl)Cl>[O:27]=[C:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:26][N:18]1[C:15]1[CH:16]=[CH:17][C:12]([CH:7]([CH3:11])[C:8]([OH:10])=[O:9])=[CH:13][CH:14]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 962WaterHCID 12917675HCID 12917675, compound

Product 1

HCID 3718IndoprofenYield 99.8%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

Acetic acid (2 ml), 8 mg of anhydrous copper sulfate and 120 mg of zinc powder were added to 148 mg of α-methylthio-α-[p-(1-oxo-2-isoindolinyl)phenyl]propionic acid, and the mixture was heated under reflux for 5 hours. Conc. hydrochloric acid was added to adjust the pH of the mixture to 1. Water (20 ml) and 20 ml of methylene chloride were added, and the insoluble matter was separated by filtration. The filtrate was extracted four times with 20 ml of methylene chloride. The organic layer was washed with 10 ml of water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford 124 mg of α-[p-(1-oxo-2-isoindolinyl)phenyl]propionic acid as colorless crystals in a yield of 99.8%. Recrystallization of the resulting product from ethanol afforded crystals having a melting point of 205° to 208° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. customthe insoluble matter was separated by filtration
  4. extractionThe filtrate was extracted four times with 20 ml of methylene chloride
  5. washThe organic layer was washed with 10 ml of water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8a95804ae1e34269b91ac85ac23e09c4
Source dataset
uspto-grants-1981_12
Patent number
US04308208

Reaction notes

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