Hydrochloric Acid → HCID 19915159, compound

HRID 1090394Notes

Reaction equation

HRID 1090394 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH:9]2[CH2:13][CH2:12][CH:11]([N:14]3C(=O)C4C(=CC=CC=4)C3=O)[CH2:10]2)=[C:4]([F:25])[CH:3]=1.[ClH:26]>C(O)C>[ClH:26].[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH:9]2[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10]2)=[C:4]([F:25])[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 14770834HCID 14770834, compound

Product 1

HCID 19915159HCID 19915159, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 20.3 g (50 mmol) of 2-[3-(4-bromo-2,5-difluorophenyl)cyclopentyl]-1H-isoindole-1,3-(2H)-dione in 100 ml of concentrated hydrochloric acid and 100 ml of ethanol was heated at reflux for 4 hours. The ethanol was allowed to evaporate and the aqueous acid mixture was heated at reflux for 4 additional hours. The solution was filtered through a fiber glass pad to remove some insoluble material and the filtrate was evaporated in vacuo. The residue was triturated with ethanol which was also removed in vacuo to give 13.1 g of the title compound.

Workup

  1. temperatureat reflux for 4 hours
  2. customto evaporate
  3. temperaturethe aqueous acid mixture was heated
  4. temperatureat reflux for 4 additional hours
  5. filtrationThe solution was filtered through a fiber glass pad
  6. customto remove some insoluble material
  7. customthe filtrate was evaporated in vacuo
  8. customThe residue was triturated with ethanol which
  9. customwas also removed in vacuo

Sources & evidence

ORD record
ord-ac18810f25a7452aa402871b13c36ed5
Source dataset
uspto-grants-1992_01
Patent number
US05081254

Reaction notes

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