m-Chloroperbenzoic acid → 8-benzyloxy-2-ethyl-1-methyl-5-oxido-1H-imidazo[4,5-c]quinoline

HRID 598306Notes

Reaction equation

HRID 598306 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH2:12]([O:19][C:20]1[CH:29]=[CH:28][C:27]2[N:26]=[CH:25][C:24]3[N:30]=[C:31]([CH2:34][CH3:35])[N:32]([CH3:33])[C:23]=3[C:22]=2[CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)(Cl)Cl>[CH2:12]([O:19][C:20]1[CH:29]=[CH:28][C:27]2[N+:26]([O-:9])=[CH:25][C:24]3[N:30]=[C:31]([CH2:34][CH3:35])[N:32]([CH3:33])[C:23]=3[C:22]=2[CH:21]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 670509308-benzyloxy-2-ethyl-1-methyl-1H-imidazo[4,5-c]quinoline

Product 1

HCID 670509858-benzyloxy-2-ethyl-1-methyl-5-oxido-1H-imidazo[4,5-c]quinolineYield 8.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A modification of the general method described in Part B of Example 3 was followed. mCPBA (60% pure, 1.39 g, 47.3 mmol) was added in portions to a solution of 8-benzyloxy-2-ethyl-1-methyl-1H-imidazo[4,5-c]quinoline (1.5 g, 47 mmol) in chloroform (75 mL), and the reaction was stirred for 5.5 hours. During the work-up, the combined aqueous washings were extracted with dichloromethane, and the product precipitated from solution. The combined dichloromethane and chloroform solutions were concentrated under reduced pressure until crystals formed and then allowed to stand overnight. The crystals were isolated by filtration. The aqueous solution was extracted with chloroform, and the combined extracts were washed with water (2×) and concentrated under reduced pressure to a small volume. Hexanes were added, and the resulting crystals were isolated by filtration. The mother liquor was concentrated under reduced pressure to afford a solid that was recrystallized from 2-propanol. The three batches of crystals were combined to yield 1.30 g of 8-benzyloxy-2-ethyl-1-methyl-5-oxido-1H-imidazo[4,5-c]quinoline.

Workup

  1. extractionDuring the work-up, the combined aqueous washings were extracted with dichloromethane
  2. customthe product precipitated from solution
  3. concentrationThe combined dichloromethane and chloroform solutions were concentrated under reduced pressure until crystals
  4. customformed
  5. waitto stand overnight
  6. customThe crystals were isolated by filtration
  7. extractionThe aqueous solution was extracted with chloroform
  8. washthe combined extracts were washed with water (2×)
  9. concentrationconcentrated under reduced pressure to a small volume
  10. additionHexanes were added
  11. customthe resulting crystals were isolated by filtration
  12. concentrationThe mother liquor was concentrated under reduced pressure
  13. customto afford a solid
  14. customthat was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-4fdb0c135be54c5c873887cb256243e1
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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