2,4-Difluoroaniline → 2-(2,4-Difluorophenyl)hexahydro-1H-isoindole-1,3(2H)-dione

HRID 1288040Notes

Reaction equation

HRID 1288040 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[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>[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[N:4]1[C:16](=[O:17])[CH:11]2[CH:10]([CH2:15][CH2:14][CH2:13][CH2:12]2)[C:19]1=[O:18]

Participants

4

Reactant 2

HCID 97092,4-DifluoroanilineHCID 85689Hexahydrophthalic anhydride

Product 1

HCID 203846662-(2,4-Difluorophenyl)hexahydro-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

8.38 Parts of 2,4-difluoroaniline were added to a solution of 10 parts of cyclohexane-1,2-dicarboxylic anhydride in 100 parts of glacial acetic acid. The mixture was stirred for two hours. The mixture was refluxed for 20 hours and the resulting product was poured into 200 parts of ice. The resulting crystals were filtered and recrystallized twice from 70 parts of methanol at -40° C to yield 10.2 parts of white crystals of 2-(2,4-difluorophenyl)-3a,4,5,6,7,7a-hexahydro-1H-isoindole-1,3(2H)-dione melting at 117°-123° C.

Workup

  1. temperatureThe mixture was refluxed for 20 hours
  2. additionthe resulting product was poured into 200 parts of ice
  3. filtrationThe resulting crystals were filtered
  4. customrecrystallized twice from 70 parts of methanol at -40° C

Sources & evidence

ORD record
ord-d0372e577669424c8fe0a56000a0055c
Source dataset
uspto-grants-1976_10
Patent number
US03987057

Reaction notes

Loading…