Benzene → HCID 58492563、化合物

HRID 68141ノート

反応式

HRID 68141 の反応式
C1C=CC=CC=1.[CH2:7]([O:10][C:11]1[C:12]([NH2:21])=[CH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:8][CH3:9].[C:22]([CH:25]([C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=1)[C:26](OCC)=[O:27])(=O)[CH3:23].C(OCC)(=O)C>CCCCCC>[CH3:38][O:37][C:34]1[CH:35]=[CH:36][C:31]([C:25]2[C:26](=[O:27])[C:13]3[C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=4[CH:20]=[C:11]([O:10][CH2:7][CH2:8][CH3:9])[C:12]=3[NH:21][C:22]=2[CH3:23])=[CH:32][CH:33]=1

参加物

6

反応物 4

HCID 241BenzeneHCID 8857Ethyl AcetateHCID 12577863Ethyl 2-(4-methoxyphenyl)-3-oxobutanoateHCID 212799043-Propoxynaphthalen-2-ylamine

生成物 1

HCID 58492563HCID 58492563、化合物収率 72%

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

実験手順

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).

後処理

  1. additionwas added 85 mg of Amberlyst 15 (Sigma-Aldrich)
  2. temperatureThe resulting mixture was heated
  3. temperatureunder reflux for 20 hours
  4. filtrationfiltered
  5. customto remove resin
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. additionDiphenyl ether (2.8 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. customgiving an oily substance (800 mg, yield: 72%)
  15. customto crystallize
  16. customrecrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-bd794614aa9f415481ca693716300b61
出典データセット
uspto-grants-2014_09
特許番号
USRE045108E1

反応ノート

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