m-Chloroperbenzoic acid → methyl [1-(2-hydroxy-2-methylpropyl)-5-oxido-1H-imidazo[4,5-c]quinolin-2-yl]carbamate

HRID 1097609Notes

Reaction equation

HRID 1097609 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[OH:12][C:13]([CH3:34])([CH3:33])[CH2:14][N:15]1[C:27]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N:20]=[CH:19][C:18]=2[N:17]=[C:16]1[NH:28][C:29](=[O:32])[O:30][CH3:31]>ClCCl>[OH:12][C:13]([CH3:34])([CH3:33])[CH2:14][N:15]1[C:27]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N+:20]([O-:6])=[CH:19][C:18]=2[N:17]=[C:16]1[NH:28][C:29](=[O:32])[O:30][CH3:31]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86626308methyl [1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]carbamate

Product 1

HCID 86626309methyl [1-(2-hydroxy-2-methylpropyl)-5-oxido-1H-imidazo[4,5-c]quinolin-2-yl]carbamateYield 76.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloroperoxybenzoic acid (1.83 g of approximately 75% pure material) was added to a stirred solution of methyl [1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]carbamate (1.0 g, 3.18 mmol) in dichloromethane (25 mL), and the reaction was stirred for 24 hours at room temperature. A precipitate formed and was collected by filtration, washed with a minimal amount of dichloromethane, and dried to provide 0.8 g of methyl [1-(2-hydroxy-2-methylpropyl)-5-oxido-1H-imidazo[4,5-c]quinolin-2-yl]carbamate as a solid.

Workup

  1. customA precipitate formed
  2. filtrationwas collected by filtration
  3. washwashed with a minimal amount of dichloromethane
  4. customdried

Sources & evidence

ORD record
ord-a0f3ae7a0dcb4323bcd7418b1f221522
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

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