反応 #155320

反応方程式

3-propoxynaphthalen-2-ylamine

ethyl α-(hydroxymethylene)-4-methoxyphenylacetate

→

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

収率 42.4%

溶媒

benzene

反応条件

後処理

1. 1
   workup.ADDITIONwas added 350 mg of Amberlyst 15 (Sigma-Aldrich)
2. 2
   温度The resulting mixture was heated
3. 3
   温度under reflux for 21 hours
4. 4
   ろ過filtered
5. 5
   その他to remove resin
6. 6
   濃縮the filtrate was concentrated under reduced pressure
7. 7
   workup.ADDITIONDiphenyl ether (2.2 ml) was added to the residue
8. 8
   温度the mixture was then heated with a mantle heater
9. 9
   温度under reflux
10. 10
    その他The resulting reaction mixture
11. 11
    温度was cooled to room temperature
12. 12
    その他directly purified
13. 13
    濃縮The purified product was concentrated under reduced pressure
14. 14
    その他to recrystallize the residue from ethyl acetate-n-hexane

実験手順

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%).

出典