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Dichloromethane → [3-(6,7-Dimethoxy-quinolin-4-yloxy)-6-methyl-pyridin-2-yl]-(6-methyl-pyridin-2-yl)-methanone

HRID 228757
Notes
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Reaction equation

HRID 228757 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[C:17]([CH:23]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[N:26]=2)[OH:24])=[N:18][C:19]([CH3:22])=[CH:20][CH:21]=1.ClCCl>CO.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[C:17]([C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[N:26]=2)=[O:24])=[N:18][C:19]([CH3:22])=[CH:20][CH:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 23078288[3-(6,7-Dimethoxy-quinolin-4-yloxy)-6-methyl-pyridin-2-yl]-(6-methyl-pyridin-2-yl)-methanol

Product 1

HCID 57756361[3-(6,7-Dimethoxy-quinolin-4-yloxy)-6-methyl-pyridin-2-yl]-(6-methyl-pyridin-2-yl)-methanoneYield 30.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst
HCID 887
Methanol
Solvent

Procedure

[3-(6,7-Dimethoxy-quinolin-4-yloxy)-6-methyl-pyridin-2-yl]-(6-methyl-pyridin-2-yl)-methanol (20 mg) was dissolved in methanol (0.4 ml) and dichloromethane (1.2 ml) to prepare a solution. Manganese dioxide (300 mg) was added to the solution, and the mixture was stirred at room temperature for 6 days. The reaction solution was filtered through Celite and was then washed with chloroform and methanol. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-acetone to give the title compound (6 mg, yield 28%).

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. washwas then washed with chloroform and methanol
  3. customThe solvent was removed by distillation under the reduced pressure
  4. customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-ee470eb670034598bf689a616a957ee4
Source dataset
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07560558B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes