Acetic Acid → HCID 66620252, compound

HRID 415557Notes

Reaction equation

HRID 415557 reaction equation
[Mn]([O-])(=O)(=O)=O.[K+].[Br:7][C:8]1[CH:9]=[CH:10][C:11]2[C:12]3[N:20]([CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[C:19](SC)=[N:18][C:13]=3[CH:14]=[N:15][C:16]=2[CH:17]=1.[S:34](=[O:37])(O)[O-:35].[Na+].[C:39](O)(=O)C>O>[Br:7][C:8]1[CH:9]=[CH:10][C:11]2[C:12]3[N:20]([CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:28])[CH3:30])[C:19]([S:34]([CH3:39])(=[O:37])=[O:35])=[N:18][C:13]=3[CH:14]=[N:15][C:16]=2[CH:17]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 516875Potassium PermanganateHCID 23665763Sodium BisulfiteHCID 66620306HCID 66620306, compound

Product 1

HCID 66620252HCID 66620252, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of potassium permanganate (1.9 g, 12 mmol) in deionized water (90 mL) was added to a solution of tert-butyl 3-(7-bromo-2-(methylthio)-1H-imidazo[4,5-c]quinolin-1-yl)propylcarbamate (2.7 g, 6 mmol) in glacial acetic acid (35 mL), and the reaction was stirred at room temperature overnight. The reaction was diluted with water and treated with sodium bisulfite. The aqueous layer was separated and extracted three times with chloroform. The combined organic fractions were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 2.3 g of tert-butyl 3-(7-bromo-2-(methylsulfonyl)-1H-imidazo[4,5-c]quinolin-1-yl)propylcarbamate.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted three times with chloroform
  3. dry with materialThe combined organic fractions were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3569b32a3884473cb8d5db2e70d1a965
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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