Reaktion #438463

Reaktionsgleichung

2,6-dimethyl-1H-quinolin-4-one

phosphorus oxychloride

NaOH

Na2CO3

→

4-chloro-2,6-dimethyl-quinoline

Ausbeute 65.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling down to room temperature
2. 2
   workup.ADDITIONthe reaction mixture was poured onto ice
3. 3
   ExtraktionThe solution was extracted with CH2Cl2 (200 mL×3)
4. 4
   SonstigeThe organic layer was separated
5. 5
   Trocknendried over magnesium sulfate
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   SonstigeThe crude product was purified by column chromatography (10% ethyl acetate in n-hexane)

Vorschrift

A mixture of 2,6-dimethyl-1H-quinolin-4-one (17.3 g, 100 mmol) and phosphorus oxychloride (30 mL) was heated at 80° C. for 3 h. After cooling down to room temperature, the reaction mixture was poured onto ice. The resulting solution was carefully alkalinized to pH 8–9 with 0.5 N NaOH and saturated Na2CO3. The solution was extracted with CH2Cl2 (200 mL×3). The organic layer was separated, dried over magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography (10% ethyl acetate in n-hexane) to give 4-chloro-2,6-dimethyl-quinoline (12.4 g, 65% yield).

Quelle