反応 #155323

反応方程式

benzene

3-propoxynaphthalen-2-ylamine

ethyl α-acetyl-4-methoxyphenylacetate

Ethyl acetate

→

2-(4-methoxyphenyl)-3-methyl-5-propoxy-4H-benzo[f]quinolin-1-one

収率 72.0%

溶媒

n-hexane

反応条件

後処理

1. 1
   workup.ADDITIONwas added 85 mg of Amberlyst 15 (Sigma-Aldrich)
2. 2
   温度The resulting mixture was heated
3. 3
   温度under reflux for 20 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 (2.8 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giving an oily substance (800 mg, yield: 72%)
15. 15
    その他to crystallize
16. 16
    その他recrystallized from ethyl acetate

実験手順

To a benzene solution (38 ml) containing 3-propoxynaphthalen-2-ylamine (600 mg, 2.98 mmol) and ethyl α-acetyl-4-methoxyphenylacetate (1.41 g, 5.96 mmol) was added 85 mg of Amberlyst 15 (Sigma-Aldrich). The resulting mixture was heated under reflux for 20 hours using a Dean-Stark trap. The reaction mixture was cooled to room temperature, filtered to remove resin, and then the filtrate was concentrated under reduced pressure. Diphenyl ether (2.8 ml) was added to the residue, and the mixture was then heated with a mantle heater and stirred for 70 minutes under reflux. The resulting reaction mixture was cooled to room temperature, and then directly purified using silica gel column chromatography (dichloromethane:methanol=80:1→70:1). The purified product was concentrated under reduced pressure, giving an oily substance (800 mg, yield: 72%). Ethyl acetate and n-hexane were added to the thus-obtained oily substance to crystallize and then recrystallized from ethyl acetate, giving a pale yellow powder of 2-(4-methoxyphenyl)-3-methyl-5-propoxy-4H-benzo[f]quinolin-1-one (290 mg).

出典