m-Chloroperbenzoic acid → 1-ethoxy-5-oxido-1H-imidazo[4,5-c]quinoline

HRID 2105481Notes

Reaction equation

HRID 2105481 reaction equation
[CH2:1]([O:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:6]=[CH:5]1)[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:22].C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([O:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N+:9]([O-:22])=[CH:8][C:7]=2[N:6]=[CH:5]1)[CH3:2]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 675069551-ethoxy-1H-imidazo[4,5-c]quinoline

Product 1

HCID 675068741-ethoxy-5-oxido-1H-imidazo[4,5-c]quinolineYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1-ethoxy-1H-imidazo[4,5-c]quinoline (2.45 g, 11.5 mmol) in dichloromethane (100 mL) was cooled to approximately 0° C., and 3-chloroperoxybenzoic acid (3.85 g of approximately 77% pure material, 17 mmol) was added. The reaction was stirred for ten minutes at 0° C., stirred for three hours at room temperature, and then stirred with saturated aqueous sodium bicarbonate (35 mL) for 15 minutes. The aqueous layer was separated and extracted with dichloromethane (5×50 mL), and the combined organic fractions were dried over potassium carbonate, filtered, and concentrated under reduced pressure to provide 2.4 g of 1-ethoxy-5-oxido-1H-imidazo[4,5-c]quinoline as an orange solid.

Workup

  1. stirringstirred for three hours at room temperature
  2. customThe aqueous layer was separated
  3. extractionextracted with dichloromethane (5×50 mL)
  4. dry with materialthe combined organic fractions were dried over potassium carbonate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2a0c6f79db2c4cae9acb95cc3a9cf024
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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