Hydrochloric Acid → (2-Benzyl-3-oxo-2,3-dihydro-1H-isoindol-1-yloxy)-acetic acid

HRID 2078476Notes

Reaction equation

HRID 2078476 reaction equation
C([O:3][C:4](=[O:24])[CH2:5][O:6][CH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[N:8]1[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)C.C(=O)([O-])[O-].[K+].[K+].Cl>CO.O>[CH2:17]([N:8]1[C:9](=[O:16])[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]1[O:6][CH2:5][C:4]([OH:24])=[O:3])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 10568063HCID 10568063, compound

Product 1

HCID 10613926(2-Benzyl-3-oxo-2,3-dihydro-1H-isoindol-1-yloxy)-acetic acidYield 93%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of compound 21 (2.0 g, 6.15 mmol) in methanol (20 mL) and water (5 mL) was added potassium carbonate (1.3 g, 9.4 mmol) and the resulting reaction mixture was allowed to stir at reflux for 2 hours. The reaction mixture is poured onto 1N HCl and extracted with dichloromethane (3×100 mL) and the combined dichloromethane extracts were dried over anhydrous sodium sulfate and concentrated in vacuo to provide 1.7 g of 22 as a white solid (1.83 g theoretical, 93% yield).

Workup

  1. customthe resulting reaction mixture
  2. temperatureat reflux for 2 hours
  3. extractionextracted with dichloromethane (3×100 mL)
  4. dry with materialthe combined dichloromethane extracts were dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-545950cba41446928932a34eb20d1e45
Source dataset
uspto-grants-2011_04
Patent number
US07928246B2

Reaction notes

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