Water → HCID 14770846, compound

HRID 1090384Notes

Reaction equation

HRID 1090384 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH:12]1[CH2:16][CH2:15][CH:14]([C:17]2[C:24]([F:25])=[CH:23][C:20]([C:21]#N)=[C:19]([F:26])[CH:18]=2)[CH2:13]1.[OH2:27].S(=O)(=O)(O)[OH:29]>>[NH2:3][CH:12]1[CH2:16][CH2:15][CH:14]([C:17]2[C:24]([F:25])=[CH:23][C:20]([C:21]([OH:29])=[O:27])=[C:19]([F:26])[CH:18]=2)[CH2:13]1

Participants

4

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 14770845HCID 14770845, compound

Product 1

HCID 14770846HCID 14770846, compound

Procedure

A solution of 35.2 g (0.1 mol) of 4-[3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)cyclopentyl]-2,5-difluorobenzonitrile in 150 ml of 98% sulfuric acid was heated at 100° for 6 hours. The reaction mixture was poured onto 1.2 L of ice and water and stirred for 2 hours until the granular precipitate dispersed. The solid was removed by filtration, washed with water and the wet filter cake suspended in 200 ml of concentrated hydrochloric acid. The suspension was heated at reflux for 8 hours and evaporated to dryness in vacuo. The residue was triturated with 250 ml of ethanol/ether (1:1); the solid was removed by filtration, washed with ethanol/ether (1:1), ether, and dried in vacuo to give 20.1 g of the title compound.

Workup

  1. additiondispersed
  2. customThe solid was removed by filtration
  3. washwashed with water
  4. temperatureThe suspension was heated
  5. temperatureat reflux for 8 hours
  6. customevaporated to dryness in vacuo
  7. customThe residue was triturated with 250 ml of ethanol/ether (1:1)
  8. customthe solid was removed by filtration
  9. washwashed with ethanol/ether (1:1), ether
  10. customdried in vacuo

Sources & evidence

ORD record
ord-9f940a552fe746d7afa6445ca359f17b
Source dataset
uspto-grants-1992_01
Patent number
US05081254

Reaction notes

Loading…