Réaction #155320

Équation de réaction

3-propoxynaphthalen-2-ylamine

ethyl α-(hydroxymethylene)-4-methoxyphenylacetate

→

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

Rendement 42.4%

Solvants

benzene

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added 350 mg of Amberlyst 15 (Sigma-Aldrich)
2. 2
   TempératureThe resulting mixture was heated
3. 3
   Températureunder reflux for 21 hours
4. 4
   Filtrationfiltered
5. 5
   Autreto remove resin
6. 6
   Concentrationthe filtrate was concentrated under reduced pressure
7. 7
   workup.ADDITIONDiphenyl ether (2.2 ml) was added to the residue
8. 8
   Températurethe mixture was then heated with a mantle heater
9. 9
   Températureunder reflux
10. 10
    AutreThe resulting reaction mixture
11. 11
    Températurewas cooled to room temperature
12. 12
    Autredirectly purified
13. 13
    ConcentrationThe purified product was concentrated under reduced pressure
14. 14
    Autreto recrystallize the residue from ethyl acetate-n-hexane

Mode opératoire

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%).

Source