Potassium Carbonate → 2-(3-Methylphenyl)-6-methoxyquinoline

HRID 40431

Reaktionsgleichung

Reaktionsgleichung von HRID 40431
B([O-])([O-])O[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[CH:4]=1.Cl[C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:23][CH3:24])[CH:19]=2)[N:14]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[CH3:9][C:5]1[CH:4]=[C:3]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:23][CH3:24])[CH:19]=3)[N:14]=2)[CH:8]=[CH:7][CH:6]=1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 836472-Chloro-6-methoxyquinolineHCID 866123723-Methylphenyl borate

Produkt 1

HCID 588711762-(3-Methylphenyl)-6-methoxyquinoline

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

3-Methylphenyl borate (1.3 mmol), 2-chloro-6-methoxyquinoline (1 mmol), tetrakis(triphenylphosphine) palladium(O) (0.05 mmol) and potassium carbonate (3 mmol) were dissolved in THF (30 mL) and H2O (10 mL). The resulting solution was stirred in a bath at 100° C. for 24 hours. After completion of the reaction, the solvents were removed. The reaction mixture was extracted with dichloromethane and water and distilled under reduced pressure. The resulting residue was purified by silica gel column chromatography. The eluate was distilled under reduced pressure. The residue was recrystallized from dichloromethane and petroleum ether, and filtered to yield 2-(3-methylphenyl)-6-methoxyquinoline as a solid.

Aufarbeitung

  1. customAfter completion of the reaction
  2. customthe solvents were removed
  3. extractionThe reaction mixture was extracted with dichloromethane and water
  4. distillationdistilled under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography
  6. distillationThe eluate was distilled under reduced pressure
  7. customThe residue was recrystallized from dichloromethane and petroleum ether
  8. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-457694425c8b4e2bb48d37dcff1b7b13
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530059B2

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