m-Chloroperbenzoic acid → HCID 68534464, compound

HRID 1992578Notes

Reaction equation

HRID 1992578 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH2:12]([C:15]1[N:16]([CH2:28][CH2:29][CH2:30][O:31][N:32]2[C:40](=[O:41])[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:33]2=[O:42])[C:17]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N:20]=[CH:19][C:18]=2[N:27]=1)[CH2:13][CH3:14]>C(Cl)(Cl)Cl>[O-:6][N+:20]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=2[C:17]2[N:16]([CH2:28][CH2:29][CH2:30][O:31][N:32]3[C:40](=[O:41])[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[C:33]3=[O:42])[C:15]([CH2:12][CH2:13][CH3:14])=[N:27][C:18]=2[CH:19]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid3×HCID 68537604HCID 68537604, compound

Product 1

HCID 68534464HCID 68534464, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-Chloroperoxybenzoic acid (14.9 g, 66.4 mmol)(mCPBA, available as an approximately 77% pure mixture) was added to a solution of 2-[3-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)propoxy]-1H-isoindole-1,3(2H)-dione (25.0 g, 60.3 mmol) in chloroform (200 mL), and the reaction was stirred for seven hours at room temperature. An analysis by liquid chromatography/mass spectrometry (LC/MS) indicated that the reaction was incomplete, and additional mCPBA (4.96 g, 22.1 mmol) was added. The reaction was allowed to stir at room temperature overnight. The solution was then washed with brine (2×100 mL) and saturated aqueous sodium bicarbonate (2×100 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide a fluffy, light-brown solid. The solid was dried under high vacuum for one hour to provide 25.7 g of 2-[3-(5-oxido-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)propoxy]-1H-isoindole-1,3(2H)-dione as a white solid.

Workup

  1. stirringto stir at room temperature overnight
  2. washThe solution was then washed with brine (2×100 mL) and saturated aqueous sodium bicarbonate (2×100 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto provide a fluffy, light-brown solid
  7. customThe solid was dried under high vacuum for one hour

Sources & evidence

ORD record
ord-4bdcd18c296041bda949628b775660fa
Source dataset
uspto-grants-2010_01
Patent number
US07648997B2

Reaction notes

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