Water → Propyl 3-(7-benzyloxy-6-methoxy-quinolin-4-yloxy)naphthalene-2-carboxylate

HRID 228918Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 228918
[OH:1][C:2]1[C:3]([C:12]([O:14][CH2:15][CH2:16][CH3:17])=[O:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH2:18]([O:25][C:26]1[CH:35]=[C:34]2[C:29]([C:30](Cl)=[CH:31][CH:32]=[N:33]2)=[CH:28][C:27]=1[O:37][CH3:38])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[CH2:18]([O:25][C:26]1[CH:35]=[C:34]2[C:29]([C:30]([O:1][C:2]3[C:3]([C:12]([O:14][CH2:15][CH2:16][CH3:17])=[O:13])=[CH:4][C:5]4[C:10]([CH:11]=3)=[CH:9][CH:8]=[CH:7][CH:6]=4)=[CH:31][CH:32]=[N:33]2)=[CH:28][C:27]=1[O:37][CH3:38])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 250121Propyl 2-hydroxy-3-naphthoateHCID 226465627-(Benzyloxy)-4-chloro-6-methoxyquinoline

Produkt 1

HCID 23078401Propyl 3-(7-benzyloxy-6-methoxy-quinolin-4-yloxy)naphthalene-2-carboxylateAusbeute 50,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Propyl 3-hydroxy-naphthalene-2-carboxylate (460 mg), 7-benzyloxy-4-chloro-6-methoxyquinoline (200 mg), and 4-dimethylaminopyridine (244 mg) were suspended in o-dichlorobenzene (4 ml), and the mixture was stirred at 120° C. for 5 hr. The reaction solution was cooled to room temperature, water was then 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, the solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-acetone to give propyl 3-(7-benzyloxy-6-methoxy-quinolin-4-yloxy)-naphthalene-2-carboxylate (165 mg, yield 50%).

Aufarbeitung

  1. temperatureThe reaction solution was cooled to room temperature
  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

Quellen und Nachweise

ORD-Eintrag
ord-168e7c6ed7eb4d059e106f9b82f305a0
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

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