m-Chloroperbenzoic acid → HCID 86626640, compound

HRID 2404979Notes

Reaction equation

HRID 2404979 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH2:12]([C:14]1[N:15]([CH2:27][C:28]#[CH:29])[C:16]2[C:25]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:19]=[CH:18][C:17]=2[N:26]=1)[CH3:13]>C(Cl)(Cl)Cl>[CH2:12]([C:14]1[N:15]([CH2:27][C:28]#[CH:29])[C:16]2[C:25]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N+:19]([O-:6])=[CH:18][C:17]=2[N:26]=1)[CH3:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86626641HCID 86626641, compound

Product 1

HCID 86626640HCID 86626640, compoundYield 111.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

3-Chloroperoxybenzoic acid (1.21 g of 77%, 1.15 eq.) was added in a single portion to a solution of 2-ethyl-1-(2-propynyl)-1H-imidazo[4,5-c]quinoline (1.00 g, 4.25 mmol, 1.0 eq) in chloroform (42 mL). The reaction mixture was stirred at ambient temperature for 1 hour at which time analysis by thin layer chromatography (TLC) indicated that the reaction was complete. The reaction mixture was diluted with chloroform (150 mL) and washed with aqueous saturated sodium bicarbonate (2×50 mL). The combined aqueous layers were back extracted with chloroform (3×30 mL). The combined organics were dried over magnesium sulfate and concentrated under reduced pressure to provide 1.19 g of 2-ethyl-1-(2-propynyl)-1H-imidazo[4,5-c]quinoline 5-oxide as a white solid.

Workup

  1. washwashed with aqueous saturated sodium bicarbonate (2×50 mL)
  2. extractionThe combined aqueous layers were back extracted with chloroform (3×30 mL)
  3. dry with materialThe combined organics were dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e25f7d37e2854d5e8d909ed5a27f1bb5
Source dataset
uspto-grants-2014_08
Patent number
US08802853B2

Reaction notes

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