m-Chloroperbenzoic acid → HCID 68534464, compound

HRID 1187390Notes

Reaction equation

HRID 1187390 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 nL), 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 nL)
  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-e5d36b54e4e94c7783e4bffb21628414
Source dataset
uspto-grants-2014_03
Patent number
US08673932B2

Reaction notes

Loading…