Ethyl Acetate → 2,5-Dichloro-4-methoxyquinoline

HRID 430090Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 430090
[Cl:1][C:2]1[CH:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[Cl:13])[N:3]=1.[O:14]([CH3:16])[K].CCOC(C)=O>CO>[Cl:1][C:2]1[CH:11]=[C:10]([O:14][CH3:16])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[Cl:13])[N:3]=1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 183536682,4,5-TrichloroquinolineHCID 178502595HCID 178502595, Verbindung

Produkt 1

HCID 183537032,5-Dichloro-4-methoxyquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To 2.4,5-trichloroquinoline (0.79 g, 3.4 mmol) was added KOMe (20.4 ml of a 0.5 M suspension in MeOH). The mixture was heated under reflux for 2.5 h. EtOAc was added and the solution was allowed to cool to room temperature. The solvent was evaporated in vacuo and the residue submitted to column chromatography (silica gel, EtOAc:hexanes 1:6→1:3). 4,5-Dichloro-2-methoxyquinoline eluted first, then 2,4,5-trichloroquinoline. followed by the title compound, a colourless solid, (0.43 g, 44%). δH (CDCl3) 4.04 (s, 3H), 6.77 (s, 1H), 7.50-7.60 (m, 2H), 7.85 (dd, J=6.7, 3.0, 1H); MS (AP+) 228 (MH+, 100%).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2.5 h
  3. customThe solvent was evaporated in vacuo
  4. wash4,5-Dichloro-2-methoxyquinoline eluted first

Quellen und Nachweise

ORD-Eintrag
ord-92851fa35ffa4a28b7a52e576c33192d
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06320051B1

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