Water → Indoprofen

HRID 1660449Notes

Reaction equation

HRID 1660449 reaction equation
CS[C:3]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:18](=O)[C:17]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]3[C:15]2=[O:24])=[CH:10][CH:9]=1)([CH3:7])[C:4]([OH:6])=[O:5].C(Cl)Cl.O>C(O)(=O)C.[Zn].S([O-])([O-])(=O)=O.[Cu+2]>[O:24]=[C:15]1[C:16]2[C:17](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][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 962WaterHCID 6344DichloromethaneHCID 12917673HCID 12917673, compound

Product 1

HCID 3718IndoprofenYield 98%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24462Copper SulfateCatalystHCID 176Acetic AcidSolvent

Procedure

α-Methylthio-α-(p-phthalimidophenyl)propionic acid (123 mg), 300 mg of zinc powder and 16 mg of anhydrous copper sulfate were stirred in 1.5 ml of acetic acid at the refluxing temperature for 5 hours. After cooling, 30 ml of methylene chloride and 20 ml of water were added, and the insoluble precipitate was separated by filtration. The filtrate was adjusted to pH 1 with conc. hydrochloric acid, and extracted three times with 20 ml of methylene chloride. The organic layer was washed with 10 ml of water, and dried with anhydrous sodium sulfate, and the solvent was evaporated off under reduced pressure to afford 99 mg of α-[p-(1-oxo-2-isoindolinyl)phenyl]propionic acid in a yield of 98%.

Workup

  1. temperatureAfter cooling
  2. customthe insoluble precipitate was separated by filtration
  3. extractionextracted three times with 20 ml of methylene chloride
  4. washThe organic layer was washed with 10 ml of water
  5. dry with materialdried with anhydrous sodium sulfate
  6. customthe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-f0dc4842582c49168f51ccdba19311cc
Source dataset
uspto-grants-1981_12
Patent number
US04308208

Reaction notes

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