m-Chloroperbenzoic acid → HCID 22478993, compound

HRID 1837592Notes

Reaction equation

HRID 1837592 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[N:12]1([CH2:25][CH2:26][CH2:27][NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[C:24]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]=[CH:16][C:15]=2[N:14]=[CH:13]1>C(Cl)(Cl)Cl>[O-:6][N+:17]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=2[C:24]2[N:12]([CH2:25][CH2:26][CH2:27][NH:28][C:29](=[O:35])[O:30][C:31]([CH3:32])([CH3:34])[CH3:33])[CH:13]=[N:14][C:15]=2[CH:16]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22478995HCID 22478995, compound

Product 1

HCID 22478993HCID 22478993, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-Chloroperoxybenzoic acid (3.71 g of ˜60%, 13.48 mmol) was added in small portions over a period of 20 minutes to a solution of tert-butyl 3-(1H-imidazo[4,5-c]quinolin-1-yl)propylcarbamate (4.0 g, 12.25 mmol) in chloroform (175 mL). After 1 hour the reaction was quenched with aqueous 1% sodium carbonate solution. The layers were separated. The organic layer was washed with aqueous 1% sodium carbonate solution (3×100 mL). The aqueous layer was extracted with chloroform (2×100 mL). The organic layers were combined and concentrated under reduced pressure to provide crude tert-butyl 3-(5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)propylcarbamate.

Workup

  1. customAfter 1 hour the reaction was quenched with aqueous 1% sodium carbonate solution
  2. customThe layers were separated
  3. washThe organic layer was washed with aqueous 1% sodium carbonate solution (3×100 mL)
  4. extractionThe aqueous layer was extracted with chloroform (2×100 mL)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dd93cb8a4c6e47abb9d49b2b586b4105
Source dataset
uspto-grants-2004_08
Patent number
US06784188B2

Reaction notes

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