m-Chloroperbenzoic acid → HCID 21075803, compound

HRID 1373890Notes

Reaction equation

HRID 1373890 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][CH2:23][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][CH2:23][CH2:24][CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 21075801HCID 21075801, compound

Product 1

HCID 21075803HCID 21075803, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-benzyl(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)amine (427 mg, 1.29 mmol) in 20 mL of CH2Cl2 was treated with MCPBA (77% max., 325 mg, 1.41 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 was dried over Na2SO4, filtered and concentrated to give N-benzyl(2-butyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)amine (393 mg) as a light brown foam.

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 was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fb59ec2d5d454d58badc3efd7e38e6bf
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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