2,4-Difluoroaniline → 2-(2,4-Difluorophenyl)-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione

HRID 1414370Notes

Reaction equation

HRID 1414370 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2[CH2:7][CH2:8][CH2:9][CH2:10][C:2]1=2.[F:12][C:13]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:14]=1[NH2:15]>C(O)(=O)C>[F:12][C:13]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:14]=1[N:15]1[C:1](=[O:11])[C:2]2[CH2:10][CH2:9][CH2:8][CH2:7][C:3]=2[C:4]1=[O:6]

Participants

4

Reactant 2

HCID 97092,4-DifluoroanilineHCID 124753,4,5,6-Tetrahydrophthalic anhydride

Product 1

HCID 214268102-(2,4-Difluorophenyl)-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 5 parts of 3,4,5,6-tetrahydrophthalic anhydride in 100 parts of glacial acetic acid was treated with 4.3 parts of 2,4-difluoroaniline at once and stirred for one hour. After refluxing for 20 hours, the reaction mixture was poured over 200 parts of ice. The resulting crystals were filtered and recrystallized from 70 parts of methanol at -40°C to yield 5 parts off-white crystals of 2-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione melting at 73°-74°C.

Workup

  1. temperatureAfter refluxing for 20 hours
  2. additionthe reaction mixture was poured over 200 parts of ice
  3. filtrationThe resulting crystals were filtered
  4. customrecrystallized from 70 parts of methanol at -40°C

Sources & evidence

ORD record
ord-50a117744c0d4c0ba571f28cddb07b2d
Source dataset
uspto-grants-1977_01
Patent number
US04001272

Reaction notes

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