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

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%).

1. additionwas added 350 mg of Amberlyst 15 (Sigma-Aldrich)
2. temperatureThe resulting mixture was heated
3. temperatureunder reflux for 21 hours
4. filtrationfiltered
5. customto remove resin
6. concentrationthe filtrate was concentrated under reduced pressure
7. additionDiphenyl ether (2.2 ml) was added to the residue
8. temperaturethe mixture was then heated with a mantle heater
9. temperatureunder reflux
10. customThe resulting reaction mixture
11. temperaturewas cooled to room temperature
12. customdirectly purified
13. concentrationThe purified product was concentrated under reduced pressure
14. customto recrystallize the residue from ethyl acetate-n-hexane

ORDレコード

ord-a5fcd6cafa3c4afd8240a21f97a07196

出典データセット

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08304546B2