m-Chloroperbenzoic acid → HCID 21075785, compound

HRID 1373887Notes

Reaction equation

HRID 1373887 reaction equation
[CH2:1]([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)[CH2:2][CH2:3][CH3:4].ClC1C=C(C=CC=1)C(OO)=[O:27]>C(Cl)Cl>[CH2:1]([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-:27])=[CH:9][C:8]=2[N:17]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 21075783HCID 21075783, compound

Product 1

HCID 21075785HCID 21075785, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)isopropylamine (334 mg, 1.18 mmol) in 10 mL of CH2Cl2 was treated with 3-chloroperoxybenzoic acid (MCPBA) (77% max., 334 mg, 1.45 mmol). After stirring for 3 h, the reaction was quenched with saturated NaHCO3 solution and extracted into CH2Cl2. The organic portion was washed with saturated NaHCO3 solution, H2O and brine. The organic portion was dried over Na2SO4, filtered and concentrated to give N-(2-butyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)isopropylamine (338 mg) as a light brown solid.

Workup

  1. customthe reaction was quenched with saturated NaHCO3 solution
  2. extractionextracted into CH2Cl2
  3. washThe organic portion was washed with saturated NaHCO3 solution, H2O and brine
  4. dry with materialThe organic portion was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e18416f4c79c48e9825bc1956a50bcb1
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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