1-(2-Hydroxy-5-methoxyphenyl)ethan-1-one → [2-(7-Benzyloxy-6-methoxyquinolin-4-yloxy)-5-methoxyphenyl]-ethanone

HRID 228906

Reaktionsgleichung

Reaktionsgleichung von HRID 228906
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[OH:12])=[O:3].[CH2:13]([O:20][C:21]1[CH:30]=[C:29]2[C:24]([C:25](Cl)=[CH:26][CH:27]=[N:28]2)=[CH:23][C:22]=1[O:32][CH3:33])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[CH2:13]([O:20][C:21]1[CH:30]=[C:29]2[C:24]([C:25]([O:12][C:5]3[CH:6]=[CH:7][C:8]([O:10][CH3:11])=[CH:9][C:4]=3[C:2](=[O:3])[CH3:1])=[CH:26][CH:27]=[N:28]2)=[CH:23][C:22]=1[O:32][CH3:33])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Komponenten

5

Edukt 2

HCID 697141-(2-Hydroxy-5-methoxyphenyl)ethan-1-oneHCID 226465627-(Benzyloxy)-4-chloro-6-methoxyquinoline

Produkt 1

HCID 23156581[2-(7-Benzyloxy-6-methoxyquinolin-4-yloxy)-5-methoxyphenyl]-ethanoneAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 72391,2-DichlorobenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

2-Hydroxy-5-methoxyacetophenone (3.00 g), 7-benzyloxy-4-chloro-6-methoxyquinoline (6.65 g), and 4-dimethylaminopyridine (4.90 g) were suspended in o-dichlorobenzene (30 ml), and the suspension was stirred at 180° C. for 2 hr. The reaction solution was cooled to room temperature, and the solvent was then removed by distillation under the reduced pressure. Water was added to the residue, and the mixture was extracted with chloroform. The chloroform layer was then washed with water and saturated brine and was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-chloroform to give 1-[2-(7-benzyloxy-6-methoxy-quinolin-4-yloxy)-5-methoxy-phenyl]-ethanone (2.53 g, yield 59%).

Aufarbeitung

  1. temperatureThe reaction solution was cooled to room temperature
  2. customthe solvent was then removed by distillation under the reduced pressure
  3. additionWater was added to the residue
  4. extractionthe mixture was extracted with chloroform
  5. washThe chloroform layer was then washed with water and saturated brine
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under the reduced pressure
  8. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0e4d680ea74640979d2e5a29d86407a8
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

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