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

HRID 2078481Notes

Reaction equation

HRID 2078481 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-0758f8a1dd6544efbc959c4a843717a0
Source dataset
uspto-grants-2011_04
Patent number
US07928246B2

Reaction notes

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