تفاعل #155323

معادلة التفاعل

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

المردود 72.0%

المذيبات

n-hexane

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added 85 mg of Amberlyst 15 (Sigma-Aldrich)
2. 2
   درجة الحرارةThe resulting mixture was heated
3. 3
   درجة الحرارةunder reflux for 20 hours
4. 4
   ترشيحfiltered
5. 5
   أخرىto remove resin
6. 6
   تركيزthe filtrate was concentrated under reduced pressure
7. 7
   workup.ADDITIONDiphenyl ether (2.8 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
    أخرىgiving an oily substance (800 mg, yield: 72%)
15. 15
    أخرىto crystallize
16. 16
    أخرىrecrystallized from ethyl acetate

الإجراء التجريبي

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).

المصدر