4-Benzyloxyaniline → HCID 21753024, compound

HRID 2396047Notes

Reaction equation

HRID 2396047 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].[CH2:25]([O:32][C:33]1[CH:39]=[CH:38][C:36]([NH2:37])=[CH:35][CH:34]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:4])[C:5]1[C:6](=[CH:7][C:8]([NH:37][C:36]2[CH:35]=[CH:34][C:33]([O:32][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[CH:39][CH:38]=2)=[C:9]([NH:37][C:36]2[CH:35]=[CH:34][C:33]([O:32][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[CH:39][CH:38]=2)[CH:10]=1)[C:21]([O:23][CH3:24])=[O:22]

Participants

4

Reactant 2

HCID 228604-BenzyloxyanilineHCID 10022190HCID 10022190, compound

Product 1

HCID 21753024HCID 21753024, 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 4.8 g (24 mmol) of 4-benzyloxyaniline in 24 ml of glacial 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 dissolved while hot in ethyl acetate and filtered, then allowed to crystallize at 0°. The crystalline residue is chromatographed on silica gel with ethyl acetate/hexane 3:2 and the product fractions are concentrated by evaporation and recrystallized from ethyl acetate/hexane, yielding the title compound in the form of beige crystals, FAB-MS: 589 [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. dissolutionThe evaporation residue is dissolved while hot in ethyl acetate
  9. filtrationfiltered
  10. customto crystallize at 0°
  11. customThe crystalline residue is chromatographed on silica gel with ethyl acetate/hexane 3:2
  12. concentrationthe product fractions are concentrated by evaporation
  13. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-22316e67bd4445d09e23b80e71c6999c
Source dataset
uspto-grants-1996_02
Patent number
US05491144

Reaction notes

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