Реакция #155320

Уравнение реакции

3-propoxynaphthalen-2-ylamine

ethyl α-(hydroxymethylene)-4-methoxyphenylacetate

→

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

Выход 42.4%

Растворители

benzene

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added 350 mg of Amberlyst 15 (Sigma-Aldrich)
2. 2
   ТемператураThe resulting mixture was heated
3. 3
   Температураunder reflux for 21 hours
4. 4
   Фильтрацияfiltered
5. 5
   Другоеto remove resin
6. 6
   Концентрированиеthe filtrate was concentrated under reduced pressure
7. 7
   workup.ADDITIONDiphenyl ether (2.2 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
    Другоеto recrystallize the residue from ethyl acetate-n-hexane

Методика

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%).

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