P-Anisidine → HCID 10320817, compound

HRID 2396052Notes

Reaction equation

HRID 2396052 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>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:4])[C:5]1[C:6](=[CH:7][C:8]([NH:33][C:30]2[CH:31]=[CH:32][C:27]([O:26][CH3:25])=[CH:28][CH:29]=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

4

Reactant 2

HCID 7732P-AnisidineHCID 10022190HCID 10022190, compound

Product 1

HCID 10320817HCID 10320817, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2.4 g (6 mmol) of 4,5-bis(trimethylsilyloxy)cyclohexa-1,4-diene-1,2-dicarboxylic acid dimethyl ester (Example 1a) and 3.0 g (24 mmol) of 4-anisidine in 24 ml ofglacial acetic acid is boiled under reflux for 2 hours. The reaction mixture is cooled, the solvent is evaporated off and the dark-brown residue is dissolved in dichloromethane and the solution is washed in succession with 20 ml of 1N HCl, 50 ml of saturated NaHCO3 and twice with 20 ml of water, dried with sodium sulfate and concentrated by evaporation. The evaporation residue is chromatographed on silica gel withethyl acetate/hexane 1:1 and the product fractions are concentrated by evaporation, yielding the title compound in the form of a yellow foam, FAB-MS: 437 [M+ +H].

Workup

  1. temperatureunder reflux for 2 hours
  2. temperatureThe reaction mixture is cooled
  3. customthe solvent is evaporated off
  4. dissolutionthe dark-brown residue is dissolved in dichloromethane
  5. washthe solution is washed in succession with 20 ml of 1N HCl, 50 ml of saturated NaHCO3 and twice with 20 ml of water
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated by evaporation
  8. customThe evaporation residue is chromatographed on silica gel withethyl acetate/hexane 1:1
  9. concentrationthe product fractions are concentrated by evaporation

Sources & evidence

ORD record
ord-f26c53d66edf47a6b27ea953ac550382
Source dataset
uspto-grants-1996_02
Patent number
US05491144

Reaction notes

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