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

HRID 2047975ノート

反応式

HRID 2047975 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-0022d1feff3d4ba9aeba622d600ad133
出典データセット
uspto-grants-2013_11
特許番号
US08592593B2

反応ノート

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