Реакция #155323

Уравнение реакции

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

Выход 72.0%

Растворители

n-hexane

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added 85 mg of Amberlyst 15 (Sigma-Aldrich)
2. 2
   ТемператураThe resulting mixture was heated
3. 3
   Температураunder reflux for 20 hours
4. 4
   Фильтрацияfiltered
5. 5
   Другоеto remove resin
6. 6
   Концентрированиеthe filtrate was concentrated under reduced pressure
7. 7
   workup.ADDITIONDiphenyl ether (2.8 ml) was added to the residue
8. 8
   Температураthe mixture was then heated with a mantle heater
9. 9
   Температураunder reflux
10. 10
    ДругоеThe resulting reaction mixture
11. 11
    Температураwas cooled to room temperature
12. 12
    Другоеdirectly purified
13. 13
    КонцентрированиеThe purified product was concentrated under reduced pressure
14. 14
    Другоеgiving an oily substance (800 mg, yield: 72%)
15. 15
    Другоеto crystallize
16. 16
    Другоеrecrystallized from ethyl acetate

Методика

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).

Источник