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

HRID 68138

반응식

HRID 68138 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 462243972-(4-methoxyphenyl)-5-propoxy-4H-benzo[f]quinolin-1-one수율 42.4%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-2367e7ee6668415aa1e6575417a21c95
출처 데이터셋
uspto-grants-2014_09
특허 번호
USRE045108E1

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