Acetic Acid → HCID 10320817, compound

HRID 1376776Notes

Reaction equation

HRID 1376776 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH2:10][C:9](O[Si](C)(C)C)=[C:8](O[Si](C)(C)C)[CH2:7][C:6]=1[C:21]([O:23][CH3:24])=[O:22])=[O:4].[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][CH:28]=1.[NH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[C:41](O)(=[O:43])C>>[CH3:1][O:2][C:3](=[O:4])[C:5]1[C:6](=[CH:7][C:8]([NH:34][C:35]2[CH:40]=[CH:39][C:38]([O:43][CH3:41])=[CH:37][CH:36]=2)=[C:9]([NH:33][C:30]2[CH:31]=[CH:32][C:27]([O:26][CH3:25])=[CH:28][CH:29]=2)[CH:10]=1)[C:21]([O:23][CH3:24])=[O:22]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 6115AnilineHCID 7732P-AnisidineHCID 10022190HCID 10022190, compound

Product 1

HCID 10320817HCID 10320817, compound

Procedure

A solution of 4.8 g (12 mmol) 4,5-Bis(trimethylsilyloxy)cyclohexa-1,4-diene 1,2-dicarboxylic acid dimethyl ester (Example 1 a), 2.6 g (24 mmol) p-anisidine and 2.2 ml (24 mmol) aniline in 48 ml of glacial acetic acid is boiled under reflux for 2 hours. The reaction mixture is cooled, the solvent is evaporated and the dark-brown residue is dissolved in ethyl acetate and the solution is washed in succession with 40 ml of 1N HCl 100 ml of saturated NaHCO3 and twice with water, dried with magnesium sulfate and concentrated by evaporation. The evaporation residue is chromatographed on silica gel with ethyl acetate/hexane 1:3 and the product fractions are concentrated by evaporation. This way, in the first product fractions 4,5-bis-(4-methoxyanilino)-phthalic acid dimethyl ester is obtained in the form of a yellow foam: FAB-MS: 437 [M+ +H]. The evaporation residue of the product fractions following thereafter is recrystallized, and 4-anilino-5-(4-methoxy-anilino)-phthalic acid dimethyl ester is obtained in the form of yellow crystals, m.p. 122°-4° C., FAB-MS: 407 [M+ +H].

Workup

  1. temperatureunder reflux for 2 hours
  2. temperatureThe reaction mixture is cooled
  3. customthe solvent is evaporated
  4. dissolutionthe dark-brown residue is dissolved in ethyl acetate
  5. washthe solution is washed in succession with 40 ml of 1N HCl 100 ml of saturated NaHCO3 and twice with water
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated by evaporation
  8. customThe evaporation residue is chromatographed on silica gel with ethyl acetate/hexane 1:3
  9. concentrationthe product fractions are concentrated by evaporation

Sources & evidence

ORD record
ord-27355ffb54fd42d7a093c2312292bd42
Source dataset
uspto-grants-1997_09
Patent number
US05663336

Reaction notes

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