Acetic Acid → Indoprofen

HRID 1660447Notes

Reaction equation

HRID 1660447 reaction equation
CS[C:3]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=O)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([OH:24])=O)=[CH:10][CH:9]=1)([CH3:7])[C:4]([OH:6])=[O:5].C(O)(=O)C.C(Cl)Cl>[Zn].S([O-])([O-])(=O)=O.[Cu+2].O>[O:24]=[C:22]1[C:17]2[C:16](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:15][N:14]1[C:11]1[CH:12]=[CH:13][C:8]([CH:3]([CH3:7])[C:4]([OH:6])=[O:5])=[CH:9][CH:10]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 12917674HCID 12917674, compound

Product 1

HCID 3718IndoprofenYield 85%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24462Copper SulfateCatalystHCID 962WaterSolvent

Procedure

α-Methylthio-α-[p-(o-carboxybenzoylamino)phenyl]propionic acid (130 mg), 300 mg of zinc powder and 20 mg of of anhydrous copper sulfate were added to 1.5 ml of acetic acid and the resulting mixture was heated under reflux for 5 hours with stirring. After cooling, 30 ml of methylene chloride and 20 ml of water were added. The insoluble precipitate was separated by filtration. The filtrate was acidified to a pH of 1 with conc. hydrochloric acid, and extracted three times with 20 ml of methylene chloride. The organic layer was washed with 20 ml of water, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to afford 86 mg of α-[p-(1-oxo-2-isoindolinyl)phenyl]propionic acid in a yield of 85%.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 5 hours
  3. temperatureAfter cooling
  4. customThe insoluble precipitate was separated by filtration
  5. extractionextracted three times with 20 ml of methylene chloride
  6. washThe organic layer was washed with 20 ml of water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b33536efdb824b94ac92af6883a240c9
Source dataset
uspto-grants-1981_12
Patent number
US04308208

Reaction notes

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