반응 #155323

반응 방정식

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

수율 72.0%

용매

n-hexane

반응 조건

후처리

1. 1
   workup.ADDITIONwas added 85 mg of Amberlyst 15 (Sigma-Aldrich)
2. 2
   온도The resulting mixture was heated
3. 3
   온도under reflux for 20 hours
4. 4
   여과filtered
5. 5
   기타to remove resin
6. 6
   농축the filtrate was concentrated under reduced pressure
7. 7
   workup.ADDITIONDiphenyl ether (2.8 ml) was added to the residue
8. 8
   온도the mixture was then heated with a mantle heater
9. 9
   온도under reflux
10. 10
    기타The resulting reaction mixture
11. 11
    온도was cooled to room temperature
12. 12
    기타directly purified
13. 13
    농축The purified product was concentrated under reduced pressure
14. 14
    기타giving an oily substance (800 mg, yield: 72%)
15. 15
    기타to crystallize
16. 16
    기타recrystallized from ethyl acetate

실험 절차

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).

출처