m-Chloroperbenzoic acid → HCID 69197839, compound

HRID 1373905Notes

Reaction equation

HRID 1373905 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([NH:18][CH:19]([CH3:21])[CH3:20])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:30])C=1>C(Cl)Cl>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([NH:18][CH:19]([CH3:20])[CH3:21])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N+:10]([O-:30])=[CH:9][C:8]=2[N:17]=1)[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 69205037HCID 69205037, compound

Product 1

HCID 69197839HCID 69197839, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-(2-ethoxymethy-1H-imidazo[4,5-c]quinolin-1-yl)isopropylamine (0.98 g, 3.45 mmol) in 35 mL of CH2Cl2 was treated with MCPBA (77% max., 1.10 g, 4.48 mmol). After stirring for 3 h, the reaction 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-(2-ethoxymethy-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)isopropylamine (0.93 g) as a light-orange solid.

Workup

  1. customthe reaction 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-9fbeca340f914804b26ba9af568f0ae0
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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