Sodium Carbonate → HCID 21075808, compound

HRID 1373896Notes

Reaction equation

HRID 1373896 reaction equation
[CH:1]([NH:4][N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:7]=[C:6]1[CH3:18])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:27])C=1.C([O-])([O-])=O.[Na+].[Na+]>ClCCCl>[CH:1]([NH:4][N:5]1[C:17]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:7]=[C:6]1[CH3:18])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 21075807HCID 21075807, compound

Product 1

HCID 21075808HCID 21075808, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of N-isopropyl(2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)amine (1.84 g, 7.66 mmol) dissolved in 50 mL of 1,2-dichloroethane was treated with MCPBA (77% max., 2.36 g, 9.58 mmol). After stirring for 3 h, the reaction mixture was treated with 2% Na2CO3 solution and extracted into CH2Cl2. The organic portion was washed with saturated 2% Na2CO3 solution, H2O and brine. The organic portion was dried over Na2SO4, filtered and concentrated to give N-isopropyl(2-methyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)amine (1.95 g) as a light orange solid.

Workup

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

Sources & evidence

ORD record
ord-d5d15bebd176462dad285f52ac7c6156
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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