m-Chloroperbenzoic acid → HCID 69506743, compound

HRID 2366722Notes

Reaction equation

HRID 2366722 reaction equation
C1C=C(Cl)C=C(C(OO)=O)C=1.[CH2:12]([C:14]1[N:15]([CH2:27][C:28]([CH3:35])([CH3:34])[C:29]([O:31][CH2:32]C)=[O:30])[C:16]2[C:25]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:19]=[CH:18][C:17]=2[N:26]=1)[CH3:13].ClC(Cl)(Cl)C([N:40]=C=O)=O>ClCCl>[NH2:40][C:18]1[C:17]2[N:26]=[C:14]([CH2:12][CH3:13])[N:15]([CH2:27][C:28]([CH3:35])([CH3:34])[C:29]([O:31][CH3:32])=[O:30])[C:16]=2[C:25]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N:19]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 76400Trichloroacetyl isocyanateHCID 69506738HCID 69506738, compound

Product 1

HCID 69506743HCID 69506743, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

mCPBA (4.8 g of 75%, 22 mmol) was added over a period of several minutes to a solution of ethyl 3-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2,2-dimethylpropanoate (3.6 g, 11 mmol) in dichloromethane (100 mL), which had been cooled to approximately 0° C. The reaction mixture was stirred cold for ten minutes and then for three hours at ambient temperature. The reaction mixture was then washed twice with a mixture of saturated aqueous sodium bicarbonate (34 mL) and 25% aqueous sodium hydroxide (1 mL), dried over potassium carbonate, filtered, and then cooled to 0° C. Trichloroacetyl isocyanate (1.7 mL, 14 mmol) was added, and the reaction was stirred cold for 15 minutes, warmed to ambient temperature, and stirred for one hour. The solvent was removed under reduced pressure, and the residue was dissolved in methanol (50 mL). Sodium methoxide (6.5 mL of a 25% solution in methanol, 30 mmol) was added to the resulting solution, and the reaction was stirred at ambient temperature overnight and cooled to approximately 0° C. for 30 minutes. A precipitate formed and was isolated by filtration to provide 1.2 g of methyl 3-(4-amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2,2-dimethylpropanoate.

Workup

  1. washThe reaction mixture was then washed twice with a mixture of saturated aqueous sodium bicarbonate (34 mL) and 25% aqueous sodium hydroxide (1 mL)
  2. dry with materialdried over potassium carbonate
  3. filtrationfiltered
  4. temperaturecooled to 0° C
  5. stirringthe reaction was stirred cold for 15 minutes
  6. temperaturewarmed to ambient temperature
  7. stirringstirred for one hour
  8. customThe solvent was removed under reduced pressure
  9. dissolutionthe residue was dissolved in methanol (50 mL)
  10. additionSodium methoxide (6.5 mL of a 25% solution in methanol, 30 mmol) was added to the resulting solution
  11. stirringthe reaction was stirred at ambient temperature overnight
  12. temperaturecooled to approximately 0° C. for 30 minutes
  13. customA precipitate formed
  14. customwas isolated by filtration

Sources & evidence

ORD record
ord-15c6e09dee9e4ecaa943dc8f97557245
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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