Reaktion #155323

Reaktionsgleichung

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

Ausbeute 72.0%

Lösungsmittel

n-hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added 85 mg of Amberlyst 15 (Sigma-Aldrich)
2. 2
   TemperaturThe resulting mixture was heated
3. 3
   Temperaturunder reflux for 20 hours
4. 4
   Filtrationfiltered
5. 5
   Sonstigeto remove resin
6. 6
   Einengenthe filtrate was concentrated under reduced pressure
7. 7
   workup.ADDITIONDiphenyl ether (2.8 ml) was added to the residue
8. 8
   Temperaturthe mixture was then heated with a mantle heater
9. 9
   Temperaturunder reflux
10. 10
    SonstigeThe resulting reaction mixture
11. 11
    Temperaturwas cooled to room temperature
12. 12
    Sonstigedirectly purified
13. 13
    EinengenThe purified product was concentrated under reduced pressure
14. 14
    Sonstigegiving an oily substance (800 mg, yield: 72%)
15. 15
    Sonstigeto crystallize
16. 16
    Sonstigerecrystallized from ethyl acetate

Vorschrift

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).

Quelle