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

HRID 492240Notes

Reaction equation

HRID 492240 reaction equation
C([O:3][C:4](=[O:6])[CH3:5])C.[CH2:7]([N:14]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]1[NH2:24])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+].Cl>O.CO>[C:4]([OH:6])(=[O:3])[CH3:5].[CH2:7]([N:14]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]1[NH2:24])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 67096604HCID 67096604, compound

Product 1

HCID 67096635(2-Benzyl-3-oxo-2,3-dihydro-1H-isoindol-1-ylamine)-acetic acidYield 40.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of compound 25 (300 mg, 0.92 mmol) in water (2 mL) and methanol (4 mL) was added potassium carbonate (509 mg, 3.7 mmol) and the resulting reaction mixture was allowed to stir at reflux for 2 hours. The reaction mixture was poured onto 3N HCl and extracted with dichloromethane (3×20 mL). The combined dichloromethane extracts were dried over anhydrous sodium sulfate and concentrated in vacuo to provide 110 mg of 26 as a white solid (272 mg theoretical, 40% yield).

Workup

  1. customthe resulting reaction mixture
  2. temperatureat reflux for 2 hours
  3. extractionextracted with dichloromethane (3×20 mL)
  4. dry with materialThe combined dichloromethane extracts were dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-44784df24aab45ff860fd27d0ab1242f
Source dataset
uspto-grants-2009_05
Patent number
US07531671B2

Reaction notes

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