m-Chloroperbenzoic acid → HCID 67506771, compound

HRID 2105475Notes

Reaction equation

HRID 2105475 reaction equation
[CH2:1]([O:8][N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[CH:13][C:12]=2[N:11]=[C:10]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:33]>ClCCl>[CH2:1]([O:8][N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N+:14]([O-:33])=[CH:13][C:12]=2[N:11]=[C:10]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 67506393HCID 67506393, compound

Product 1

HCID 67506771HCID 67506771, compoundYield 125.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-(Benzyloxy)-2-phenyl-1H-imidazo[4,5-c]quinoline (0.951 g, 2.71 mmol) was combined with 3-chloroperoxybenzoic acid (1.2 g of 77% pure material, 5.4 mmol) in dichloromethane (10 mL) and stirred at room temperature for 30 minutes. An analysis by liquid chromatography/mass spectrometry (LC/MS) indicated the presence of starting material; additional 3-chloroperoxybenzoic acid (0.1 g) was added. The reaction mixture was stirred for 18 hours at room temperature and then diluted with dichloromethane, washed sequentially with saturated aqueous potassium carbonate, water, and brine, dried over sodium sulfate, filtered, and then concentrated under reduced pressure to provide 1.25 g of 1-(benzyloxy)-5-oxido-2-phenyl-1H-imidazo[4,5-c]quinoline as a black oil. Attempts to obtain a solid by trituration with hexane/diethyl ether and hexane were unsuccessful.

Workup

  1. stirringThe reaction mixture was stirred for 18 hours at room temperature
  2. washwashed sequentially with saturated aqueous potassium carbonate, water, and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7fc448ffc2e44c4cafea2af24b28409f
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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