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m-Chloroperbenzoic acid → 8-benzyloxy-2-[2-methoxy(ethoxymethyl)]-1-methyl-5-oxido-1H-imidazo[4,5-c]quinolin

HRID 598309
Notes
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Reaction equation

HRID 598309 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[N:15]=[CH:14][C:13]3[N:19]=[C:20]([CH2:23][O:24][CH2:25][CH2:26][O:27][CH3:28])[N:21]([CH3:22])[C:12]=3[C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:36]C1C=CC2C3N(CC(C)C)C(C)=NC=3C=NC=2C=1)C1C=CC=CC=1.C1C=C(Cl)C=C(C(OO)=O)C=1>ClCCl>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[N+:15]([O-:36])=[CH:14][C:13]3[N:19]=[C:20]([CH2:23][O:24][CH2:25][CH2:26][O:27][CH3:28])[N:21]([CH3:22])[C:12]=3[C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 670509187-benzyloxy-2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolineHCID 670510438-benzyloxy-2-[2-methoxy(ethoxymethyl)]-1-methyl-1H-imidazo[4,5-c]quinoline

Product 1

HCID 670510018-benzyloxy-2-[2-methoxy(ethoxymethyl)]-1-methyl-5-oxido-1H-imidazo[4,5-c]quinolin

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

A modification of the general method described in Part B of Example 3 was followed using 8-benzyloxy-2-[2-methoxy(ethoxymethyl)]-1-methyl-1H-imidazo[4,5-c]quinoline (5.4 g, 14 mmol) in lieu of 7-benzyloxy-2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline. Dichloromethane (100 mL) was used as the solvent, and after three hours an analysis by TLC indicated the reaction was incomplete. Additional mCPBA (0.5 equivalents) was added, and the reaction was terminated after one additional hour. After the work-up the product was purified by column chromatography on silica gel (eluting with 90:10 dichloromethane:methanol to provide 1.5 g of 8-benzyloxy-2-[2-methoxy(ethoxymethyl)]-1-methyl-5-oxido-1H-imidazo[4,5-c]quinolin as an oil.

Workup

  1. customthe reaction was terminated after one additional hour
  2. customAfter the work-up the product was purified by column chromatography on silica gel (
  3. washeluting with 90:10 dichloromethane

Sources & evidence

ORD record
ord-47ff538f018042bca996f91bfc4627ce
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07897597B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes