m-Chloroperbenzoic acid → HCID 69203575, compound

HRID 1373902Notes

Reaction equation

HRID 1373902 reaction equation
[CH2:1]([NH: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[CH2:22][O:23][CH2:24][CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:34])C=1>C(Cl)Cl>[CH2:1]([NH:8][N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N+:14]([O-:34])=[CH:13][C:12]=2[N:11]=[C:10]1[CH2:22][O:23][CH2:24][CH3:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 69202897HCID 69202897, compound

Product 1

HCID 69203575HCID 69203575, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-benzyl-(2-ethoxymethy-1H-imidazo[4,5-c]quinolin-1-yl)amine (1.01 g, 3.04 mmol) in 50 mL of CH2Cl2 was treated with MCPBA (77% max., 1.02 g, 4.56 mmol). After stirring for 3 h, the reaction mixture was quenched with 2% Na2CO3 solution and extracted into CH2Cl2. The organic portion was washed with H2O and brine. The organic portion was dried over Na2SO4, filtered and concentrated to give N-benzyl-(2-ethoxymethy-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)amine (0.99 g) as a light-yellow solid.

Workup

  1. customthe reaction mixture was quenched with 2% Na2CO3 solution
  2. extractionextracted into CH2Cl2
  3. washThe organic portion was washed with H2O and brine
  4. dry with materialThe organic portion was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2d9471b64211492897504b35ac09c782
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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