m-Chloroperbenzoic acid → HCID 14986963, compound

HRID 1292477Notes

Reaction equation

HRID 1292477 reaction equation
[CH3:1][C:2]([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]=[CH:6]1)([CH3:4])[CH3:3].ClC1C=CC=C(C(OO)=[O:26])C=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.[OH-].[NH4+]>[CH3:4][C:2]([N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N+:10]([O-:26])=[CH:9][C:8]=2[N:7]=[CH:6]1)([CH3:1])[CH3:3]

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 14986962HCID 14986962, compound

Product 1

HCID 14986963HCID 14986963, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 23.5 g (0.104 mole) of 1-(1,1-dimethylethyl)-1H-imidazo[4,5-c]quinoline in 200 mL of chloroform was added 23.4 g (0.115 mole) of meta-chloroperbenzoic acid. The mixture was stirred at about 20° C. for 24 hours. The solution was basified with saturated sodium bicarbonate solution, then dried over magnesium sulfate. Filtration of the mixture, followed by evaporation in vacuo provided a cream colored solid. The solid residue was slurred in dilute ammonium hydroxide, then filtered, washed with water and dried, to provide white solid 1-(1,1-dimethylethyl)-1H-imidazo[4,5-c]quinoline-5-oxide.

Workup

  1. dry with materialdried over magnesium sulfate
  2. filtrationFiltration of the mixture
  3. customfollowed by evaporation in vacuo
  4. customprovided a cream
  5. filtrationfiltered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-b3efd285151d424398dd03e0169e83c5
Source dataset
uspto-grants-1998_05
Patent number
US05756747

Reaction notes

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