2,4-Dichloroquinoline → 4-Chloro-6-methoxyquinoline

HRID 333925

Reaktionsgleichung

Reaktionsgleichung von HRID 333925
Cl[C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:13][O-:14].[Na+]>C1(C)C=CC=CC=1>[Cl:12][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:14][CH3:13])[CH:8]=2)[N:3]=[CH:2][CH:11]=1

Komponenten

4

Edukt 2

HCID 6075032,4-DichloroquinolineHCID 10942334Sodium Methoxide

Produkt 1

HCID 2283484-Chloro-6-methoxyquinolineAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

2,4-Dichloroquinoline (2.5 g, 12.6 mmol) was dissolved in anhydrous toluene (20 ml), a suspension of sodium methoxide (2.5 g, 46.3 mmol) in anhydrous toluene (20 ml) was added and the mixture was heated under reflux for 16 hours. After cooling to room temperature the suspension was filtered, the filter cake washed once with toluene (50 ml), the combined filtrates were evaporated under reduced pressure to dryness to yield 2.1 g (10.8 mmol, 86%) of a red solid. MS (ES) m/z=193.1 [M+H]+.

Aufarbeitung

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 16 hours
  4. filtrationwas filtered
  5. washthe filter cake washed once with toluene (50 ml)
  6. customthe combined filtrates were evaporated under reduced pressure to dryness

Quellen und Nachweise

ORD-Eintrag
ord-ea9c16e87f9848afa81e95787bee821b
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883791B2

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