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

HRID 1874030

Reaktionsgleichung

Reaktionsgleichung von HRID 1874030
[CH2:1]([O:4][C:5]1[C:6]([NH2:15])=[CH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:2][CH3:3].[OH:16][CH:17]=[C:18]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)[C:19](OCC)=O>C1C=CC=CC=1>[CH3:31][O:30][C:27]1[CH:28]=[CH:29][C:24]([C:18]2[C:17](=[O:16])[C:7]3[C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=4[CH:14]=[C:5]([O:4][CH2:1][CH2:2][CH3:3])[C:6]=3[NH:15][CH:19]=2)=[CH:25][CH:26]=1

Komponenten

4

Edukt 2

HCID 212799043-Propoxynaphthalen-2-ylamineHCID 67418551Ethyl alpha-(hydroxymethylene)-4-methoxyphenylacetate

Produkt 1

HCID 462243972-(4-methoxyphenyl)-5-propoxy-4H-benzo[f]quinolin-1-oneAusbeute 42,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a5fcd6cafa3c4afd8240a21f97a07196
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304546B2

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