Acetic Acid → 2-(2,4,6-Trifluorophenyl)-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione

HRID 1414371Notes

Reaction equation

HRID 1414371 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.C(O)(=O)C.[F:16][C:17]1[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[C:18]=1[NH2:19]>C(Cl)Cl>[F:16][C:17]1[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[C:18]=1[N:19]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

5

Reactant 3

HCID 176Acetic Acid2×HCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 677652,4,6-Trifluoroaniline

Product 1

HCID 214268112-(2,4,6-Trifluorophenyl)-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5.3 parts of 3,4,5,6-tetrahydrophthalic anhydride in 100 parts of glacial acetic acid was treated with 5 parts of 2,4,6-trifluoroaniline at once. After refluxing for 24 hours, the acetic acid was stripped from the reaction mixture under 300 mm hg pressure. The residue was dissolved in 100 parts of methylene chloride and washed with 100 parts of 10% aqueous sodium carbonate. After drying over anhydrous sodium sulfate, the solution was stripped under 300 mm hg pressure. The resulting pink oil was crystallized from 70 parts of methanol at -40°C to yield 4.7 parts white crystals of 2-(2,4,6-trifluorophenyl)-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione melting at 91°-92°C.

Workup

  1. temperatureAfter refluxing for 24 hours
  2. washwashed with 100 parts of 10% aqueous sodium carbonate
  3. dry with materialAfter drying over anhydrous sodium sulfate
  4. customThe resulting pink oil was crystallized from 70 parts of methanol at -40°C

Sources & evidence

ORD record
ord-7afe47d64afa46509a5c38f3dce17c6c
Source dataset
uspto-grants-1977_01
Patent number
US04001272

Reaction notes

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