m-Chloroperbenzoic acid → HCID 21936588, compound

HRID 431480Notes

Reaction equation

HRID 431480 reaction equation
[CH3:1][C:2]1[N:3]([CH2:15][CH2:16][O:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:4]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[CH:6][C:5]=2[N:14]=1.ClC1C=C(C=CC=1)C(OO)=[O:33]>C(Cl)(Cl)Cl>[CH3:1][C:2]1[N:3]([CH2:15][CH2:16][O:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:26])[CH3:25])[C:4]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N+:7]([O-:33])=[CH:6][C:5]=2[N:14]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 21936603HCID 21936603, compound

Product 1

HCID 21936588HCID 21936588, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of tert-butyl 2-[2-(2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethylcarbamate (10.75 g, 29.0 mmol) in 150 mL of CHCl3 was chilled in an ice water bath. The solution was treated with 3-chloroperoxybenzoic acid (MCPBA, 70%, 10.73 g, 43.5 mmol). After stirring for 1.5 h, the reaction mixture was washed with 1% Na2CO3 (3×) solution and the layers were separated. The organic portion was washed with H2O and brine then dried over Na2SO4 and concentrated to give a sticky brown solid. The solid was triturated with ether to yield 11.21 g of tert-butyl 2-[2-(2-methyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethylcarbamate as a light tan solid.

Workup

  1. washthe reaction mixture was washed with 1% Na2CO3 (3×) solution
  2. customthe layers were separated
  3. washThe organic portion was washed with H2O and brine
  4. dry with materialthen dried over Na2SO4
  5. concentrationconcentrated
  6. customto give a sticky brown solid
  7. customThe solid was triturated with ether

Sources & evidence

ORD record
ord-be3dd53481c74bb4ba5c39fe568b9a97
Source dataset
uspto-grants-2003_12
Patent number
US06660735B2

Reaction notes

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