[2-(6,7-Dimethoxy-quinolin-4-yloxy)-5-methoxy-phenyl]-thiazol-2-yl-methanol → [2-(6,7-Dimethoxy-quinolin-4-yloxy)-5-methoxy-phenyl]-thiazol-2-yl-methanone

HRID 228726Notes

Reaction equation

HRID 228726 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[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=1[CH:24]([C:26]1[S:27][CH:28]=[CH:29][N:30]=1)[OH:25]>CO.C(Cl)Cl.[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[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=1[C:24]([C:26]1[S:27][CH:28]=[CH:29][N:30]=1)=[O:25]

Participants

4

Reactant 1

HCID 23078351[2-(6,7-Dimethoxy-quinolin-4-yloxy)-5-methoxy-phenyl]-thiazol-2-yl-methanol

Product 1

HCID 57756447[2-(6,7-Dimethoxy-quinolin-4-yloxy)-5-methoxy-phenyl]-thiazol-2-yl-methanoneYield 74%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

[2-(6,7-Dimethoxy-quinolin-4-yloxy)-5-methoxy-phenyl]-thiazol-2-yl-methanol (90 mg) was dissolved in methanol/methylene chloride (3 ml/9 ml) to prepare a solution, manganese dioxide (90 mg) was added to the solution, and the mixture was stirred at room temperature overnight. The reaction solution was filtered through Celite, water was added to the filtrate, and the mixture was extracted with ethyl acetate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-hexane to give the title compound (65 mg, yield 74%).

Workup

  1. additionwas added to the solution
  2. filtrationThe reaction solution was filtered through Celite, water
  3. additionwas added to the filtrate
  4. extractionthe mixture was extracted with ethyl acetate
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-51cdbbc4452048398e68d71c5e3c0c14
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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