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

HRID 492235Notes

Reaction equation

HRID 492235 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-0da27ae7c8694fcc91a6453b1d5e9325
Source dataset
uspto-grants-2009_05
Patent number
US07531671B2

Reaction notes

Loading…