Ammonia → 5,6-Bis[(4-fluorophenyl)amino]-1H-isoindole-1,3(2H)-dione

HRID 2396041Notes

Reaction equation

HRID 2396041 reaction equation
C[O:2][C:3](=O)[C:4]1[C:5](=[CH:10][C:11]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH:13]=1)[C:6](OC)=[O:7].[NH3:31]>C(O)CO>[F:21][C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:12]2[CH:13]=[C:4]3[C:3](=[O:2])[NH:31][C:6](=[O:7])[C:5]3=[CH:10][C:11]=2[NH:22][C:23]2[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 10476762HCID 10476762, compound

Product 1

HCID 67111545,6-Bis[(4-fluorophenyl)amino]-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

Analogously to Example 1, 290 mg (0.7 mmol) of 4,5-bis(4-fluoroanilino)phthalic acid dimethyl ester in 22 ml of ethylene glycol are heated at 120° and, with stirring, ammonia gas is passedthrough the mixture for 18 hours. The reaction mixture is cooled and extracted with ethyl acetate. The ethyl acetate phases are washed in succession three times with water and once with saturated sodium chloride solution, dried with sodium sulfate and concentrated by evaporation. The evaporation residue is chromatographed on silica gel with hexane/ethyl acetate 1:1 and the product fractions are combined and concentrated by evaporation, yielding the title compound in the form of orange crystals, m.p. >220° C., FAB-MS: 366 [M+ +H].

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate phases are washed in succession three times with water and once with saturated sodium chloride solution
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated by evaporation
  6. customThe evaporation residue is chromatographed on silica gel with hexane/ethyl acetate 1:1
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-e524e370765543e2b68578f1e0844272
Source dataset
uspto-grants-1996_02
Patent number
US05491144

Reaction notes

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