Reacción #155320

Ecuación de reacción

3-propoxynaphthalen-2-ylamine

ethyl α-(hydroxymethylene)-4-methoxyphenylacetate

→

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

Rendimiento 42.4%

Disolventes

benzene

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added 350 mg of Amberlyst 15 (Sigma-Aldrich)
2. 2
   TemperaturaThe resulting mixture was heated
3. 3
   Temperaturaunder reflux for 21 hours
4. 4
   Filtraciónfiltered
5. 5
   Otroto remove resin
6. 6
   Concentraciónthe filtrate was concentrated under reduced pressure
7. 7
   workup.ADDITIONDiphenyl ether (2.2 ml) was added to the residue
8. 8
   Temperaturathe mixture was then heated with a mantle heater
9. 9
   Temperaturaunder reflux
10. 10
    OtroThe resulting reaction mixture
11. 11
    Temperaturawas cooled to room temperature
12. 12
    Otrodirectly purified
13. 13
    ConcentraciónThe purified product was concentrated under reduced pressure
14. 14
    Otroto recrystallize the residue from ethyl acetate-n-hexane

Procedimiento

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%).

Fuente