Hydrochloric Acid → 4-Chloro-2,3-dihydro-1H-isoindole

HRID 1630Notes

Reaction equation

HRID 1630 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:9](=O)[NH:8][C:6](=O)[C:5]2=[CH:11][CH:12]=1.[ClH:13]>O1CCCC1>[Cl:13][C:11]1[CH:12]=[CH:2][CH:3]=[C:4]2[C:5]=1[CH2:6][NH:8][CH2:9]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 2312394-Chloro-phthalimide

Product 1

HCID 147958684-Chloro-2,3-dihydro-1H-isoindole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chlorophthalimide (60 g) in 1 liter of tetrahydrofuran was added borane-methyl sulfide complex (100 ml of 10M), and the mixture was refluxed overnight. After cooling, 100 ml of 6N hydrochloric acid was added slowly, the mixture refluxed for 2 hours, and then filtered. The filtrate was concentrated under reduced pressure, and the resulting aqueous solution washed with ethyl acetate. The aqueous layer was then basified with ammonium hydroxide and extracted with methylene chloride. Solvent was removed from the extract, and the residue distilled under vacuum to give 4-chloroisoindoline, a white solid, m.p. 48°-50° C.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. temperatureAfter cooling
  3. temperaturethe mixture refluxed for 2 hours
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. washthe resulting aqueous solution washed with ethyl acetate
  7. extractionextracted with methylene chloride
  8. customSolvent was removed from the extract
  9. distillationthe residue distilled under vacuum

Sources & evidence

ORD record
ord-9c7cc9bbc71144c7ae9f1e2d0e680324
Source dataset
uspto-grants-1998_03
Patent number
US05726197

Reaction notes

Loading…