Reaktion #155320

Reaktionsgleichung

3-propoxynaphthalen-2-ylamine

ethyl α-(hydroxymethylene)-4-methoxyphenylacetate

→

2-(4-methoxyphenyl)-5-propoxy-4H-benzo[f]quinolin-1-one

Ausbeute 42.4%

Lösungsmittel

benzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added 350 mg of Amberlyst 15 (Sigma-Aldrich)
2. 2
   TemperaturThe resulting mixture was heated
3. 3
   Temperaturunder reflux for 21 hours
4. 4
   Filtrationfiltered
5. 5
   Sonstigeto remove resin
6. 6
   Einengenthe filtrate was concentrated under reduced pressure
7. 7
   workup.ADDITIONDiphenyl ether (2.2 ml) was added to the residue
8. 8
   Temperaturthe mixture was then heated with a mantle heater
9. 9
   Temperaturunder reflux
10. 10
    SonstigeThe resulting reaction mixture
11. 11
    Temperaturwas cooled to room temperature
12. 12
    Sonstigedirectly purified
13. 13
    EinengenThe purified product was concentrated under reduced pressure
14. 14
    Sonstigeto recrystallize the residue from ethyl acetate-n-hexane

Vorschrift

To a benzene solution (50 ml) containing 3-propoxynaphthalen-2-ylamine (2.05 g, 10.18 mmol) and ethyl α-(hydroxymethylene)-4-methoxyphenylacetate (2.29 g, 10.3 mmol) was added 350 mg of Amberlyst 15 (Sigma-Aldrich). The resulting mixture was heated under reflux for 21 hours using a Dean-Stark trap. The reaction mixture was then cooled to room temperature, filtered to remove resin, and then the filtrate was concentrated under reduced pressure. Diphenyl ether (2.2 ml) was added to the residue, and the mixture was then heated with a mantle heater and stirred for 1.5 hours under reflux. The resulting reaction mixture was cooled to room temperature, and then directly purified using silica gel column chromatography (dichloromethane:methanol=100:1→60:1). The purified product was concentrated under reduced pressure to recrystallize the residue from ethyl acetate-n-hexane, giving a pale yellow powder of 2-(4-methoxyphenyl)-5-propoxy-4H-benzo[f]quinolin-1-one (1.55 g, yield: 42%).

Quelle