تفاعل #155320

معادلة التفاعل

3-propoxynaphthalen-2-ylamine

ethyl α-(hydroxymethylene)-4-methoxyphenylacetate

→

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

المردود 42.4%

المذيبات

benzene

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added 350 mg of Amberlyst 15 (Sigma-Aldrich)
2. 2
   درجة الحرارةThe resulting mixture was heated
3. 3
   درجة الحرارةunder reflux for 21 hours
4. 4
   ترشيحfiltered
5. 5
   أخرىto remove resin
6. 6
   تركيزthe filtrate was concentrated under reduced pressure
7. 7
   workup.ADDITIONDiphenyl ether (2.2 ml) was added to the residue
8. 8
   درجة الحرارةthe mixture was then heated with a mantle heater
9. 9
   درجة الحرارةunder reflux
10. 10
    أخرىThe resulting reaction mixture
11. 11
    درجة الحرارةwas cooled to room temperature
12. 12
    أخرىdirectly purified
13. 13
    تركيزThe purified product was concentrated under reduced pressure
14. 14
    أخرىto recrystallize the residue from ethyl acetate-n-hexane

الإجراء التجريبي

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%).

المصدر