m-Chloroperbenzoic acid → HCID 67263041, compound

HRID 2426355Notes

Reaction equation

HRID 2426355 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH3:12][C:13]([OH:37])([CH3:36])[CH2:14][N:15]1[C:27]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N:20]=[CH:19][C:18]=2[N:17]=[C:16]1[CH2:28][CH2:29][C:30]1([CH3:35])[O:34][CH2:33][CH2:32][O:31]1>C(Cl)(Cl)Cl>[CH3:36][C:13]([OH:37])([CH3:12])[CH2:14][N:15]1[C:27]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N+:20]([O-:9])=[CH:19][C:18]=2[N:17]=[C:16]1[CH2:28][CH2:29][C:30]1([CH3:35])[O:34][CH2:33][CH2:32][O:31]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 67052422HCID 67052422, compound

Product 1

HCID 67263041HCID 67263041, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

mCPBA (2.2 g of 60% pure material, 7.7 mmol) was added in portions over a period of five minutes to a stirred solution of 2-methyl-1-{2-[2-(2-methyl-1,3-dioxolan-2-yl)ethyl]-1H-imidazo[4,5-c]quinolin-1-yl}propan-2-ol (2.5 g, 7.0 mmol) in chloroform (47 mL), and the reaction was stirred at room temperature for 20 minutes. The reaction mixture was partitioned between dichloromethane (200 mL) and saturated aqueous sodium carbonate (100 mL). The organic layer was separated and washed with saturated aqueous sodium carbonate (100 mL). The combined aqueous fractions were extracted with dichloromethane (50 mL). The combined organic fractions were washed with brine (50 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide 2-methyl-1-{2-[2-(2-methyl-1,3-dioxolan-2-yl)ethyl]-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl}propan-2-ol as a tan solid.

Workup

  1. customThe reaction mixture was partitioned between dichloromethane (200 mL) and saturated aqueous sodium carbonate (100 mL)
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous sodium carbonate (100 mL)
  4. extractionThe combined aqueous fractions were extracted with dichloromethane (50 mL)
  5. washThe combined organic fractions were washed with brine (50 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-098c756bfbe9494589bb769ab1af22ca
Source dataset
uspto-grants-2011_06
Patent number
US07968563B2

Reaction notes

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