Hexahydrophthalic anhydride → 1H-Isoindole-1,3(2H)-dione, 2-(4-chloro-2-fluorophenyl)hexahydro-

HRID 47006

Reaction equation

HRID 47006 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.[CH:10]12[C:19](=O)[O:18][C:16](=[O:17])[CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15]2>C(O)(=O)C>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[C:16](=[O:17])[CH:11]3[CH:10]([CH2:15][CH2:14][CH2:13][CH2:12]3)[C:19]2=[O:18])=[C:4]([F:9])[CH:3]=1

Participants

4

Reactant 2

HCID 85689Hexahydrophthalic anhydrideHCID 938984-Chloro-2-fluoroaniline

Product 1

HCID 36258131H-Isoindole-1,3(2H)-dione, 2-(4-chloro-2-fluorophenyl)hexahydro-

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

9.44 parts of 4-chloro-2-fluoroaniline were then added to a solution of 10 parts of cyclohexane-1,2-dicarboxylic anhydride in 75 parts of glacial acetic acid. After refluxing for 6 hours, the reaction mixture was poured into 200 parts of ice. The resulting crystals were filtered and recrystallized from 70 parts of methanol at -40° to yield 12.4 parts of white crystals of 2-(4-chloro-2-fluorophenyl)-3a,4,5,6,7,7a-hexahydro-1H-isoindole-1,3(2H)dione melting at 94°-95.5°.

Workup

  1. temperatureAfter refluxing for 6 hours
  2. additionthe reaction mixture was poured into 200 parts of ice
  3. filtrationThe resulting crystals were filtered
  4. customrecrystallized from 70 parts of methanol at -40°

Sources & evidence

ORD record
ord-5909df8b36d248d0a6b3af67401690c7
Source dataset
uspto-grants-1979_11
Patent number
US04175948

Linked notes

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