Water → [3-(6,7-Dimethoxy-quinolin-4-yloxy)-6-methyl-pyridin-2-yl]-phenyl-methyl acetate

HRID 228751Notes

Reaction equation

HRID 228751 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]=[CH:27][CH:26]=2)[OH:24])=[N:18][C:19]([CH3:22])=[CH:20][CH:21]=1.C(N(CC)CC)C.[C:38](OC(=O)C)(=[O:40])[CH3:39].O>C(Cl)(Cl)Cl.CN(C)C1C=CN=CC=1>[C:38]([O:24][CH:23]([C:17]1[C:16]([O:15][C:6]2[C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=[CH:8][CH:7]=2)=[CH:21][CH:20]=[C:19]([CH3:22])[N:18]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:40])[CH3:39]

Participants

7

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 57756348[3-(6,7-Dimethoxy-quinolin-4-yloxy)-6-methyl-pyridin-2-yl]-phenyl-methanol2×

Product 1

HCID 57756548[3-(6,7-Dimethoxy-quinolin-4-yloxy)-6-methyl-pyridin-2-yl]-phenyl-methyl acetateYield 89%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

[3-(6,7-Dimethoxy-quinolin-4-yloxy)-6-methyl-pyridin-2-yl]-phenyl-methanol (47 mg) (compound 217) was dissolved in chloroform (7 ml) to prepare a solution. Triethylamine (1 ml), acetic anhydride (0.8 ml), and 4-dimethylaminopyridine (20 mg) were added to the solution, and the mixture was stirred at room temperature overnight. Water was added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was washed with saturated brine and was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under the reduced pressure. The residue was purified by thin layer chromatography using chloroform-acetone to give the title compound (48 mg, yield 89%).

Workup

  1. customto prepare a solution
  2. extractionthe mixture was extracted with chloroform
  3. washThe chloroform layer was washed with saturated brine
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customthe solvent was removed by distillation under the reduced pressure
  6. customThe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-6908cdab257b4d0d97ec811f15067026
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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