Ammonia → HCID 10318148, compound

HRID 2396051Notes

Reaction equation

HRID 2396051 reaction equation
C[O:2][C:3](=O)[C:4]1[C:5](=[CH:10][C:11]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)=[C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH:13]=1)[C:6]([O:8]C)=O.[NH3:33].[Cl-].[Na+]>C(O)CO>[CH3:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([NH:14][C:12]2[CH:13]=[C:4]3[C:3](=[O:2])[NH:33][C:6](=[O:8])[C:5]3=[CH:10][C:11]=2[NH:23][C:24]2[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 5234Sodium ChlorideHCID 10320817HCID 10320817, compound

Product 1

HCID 10318148HCID 10318148, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

Analogously to Example 1, 393 mg (0.9 mmol) of 4,5-bis(4-methoxyanilino)phthalic acid dimethyl ester in 25 ml of ethyleneglycol are heated at 120°, ammonia gas being passed through the mixture, with stirring, for 18 hours. The reaction mixture is cooled, saturated with sodium chloride and extracted with ethyl acetate. The ethylacetate 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 onsilica gel with ethyl acetate/hexane 1:1 and the product fractions are combined and concentrated by evaporation, yielding the title compound in the form of yellow crystals, m.p. 191°-193° C., FAB-MS: 390 [M+ +H].

Workup

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

Sources & evidence

ORD record
ord-93e26cbb1f4a4ff8964eac227e45ab75
Source dataset
uspto-grants-1996_02
Patent number
US05491144

Reaction notes

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