Tetrahydrofuran → 4-Methyl-7-(2-thienyl)-5,6,7,8-tetrahydroquinolin-5-one

HRID 1700493ノート

反応式

HRID 1700493 の反応式
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]1[CH2:11][C:10](=O)[CH2:9][C:8](=[O:13])[CH2:7]1.Cl.[NH2:15][CH2:16][C:17]#[C:18][CH3:19].O1CCCC1>C(N(CC)CC)C>[CH3:19][C:18]1[C:9]2[C:8](=[O:13])[CH2:7][CH:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)[CH2:11][C:10]=2[N:15]=[CH:16][CH:17]=1

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 5736855-(2-Thienyl)cyclohexane-1,3-dioneHCID 12599999But-2-yn-1-amine hydrochloride

生成物 1

HCID 109667404-Methyl-7-(2-thienyl)-5,6,7,8-tetrahydroquinolin-5-one収率 35.7%

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

実験手順

To a mixture of 5-(2-thienyl)cyclohexane-1,3-dione (1.5 g), 1-amino-2-butyne hydrochloride (0.82 g), molecular sieves 4A (3 g) and tetrahydrofuran (30 ml) was added triethylamine (0.78 g). The mixture was stirred at room temperature for 1 hour, refluxed for refluxed for 12 hours and cooled, and insoluble materials were filtered off. Under reduced pressure, the solvent was evaporated, and to the residue was added diphenylether (80 ml), and the mixture was stirred at 250° C. for 6 hours. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in ethyl acetate. The solution was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure, and the residue was purified with silica gel column chromatography (EtOAc/hexane) to give colorless crystals of 4-methyl-7-(2-thienyl)-5,6,7,8-tetrahydroquinolin-5-one (0.67 g).

後処理

  1. temperaturerefluxed
  2. temperaturefor refluxed for 12 hours
  3. temperaturecooled
  4. filtrationinsoluble materials were filtered off
  5. customUnder reduced pressure, the solvent was evaporated
  6. additionto the residue was added diphenylether (80 ml)
  7. stirringthe mixture was stirred at 250° C. for 6 hours
  8. customUnder reduced pressure, the solvent was evaporated
  9. dissolutionthe residue was dissolved in ethyl acetate
  10. washThe solution was washed with water and saturated brine
  11. dry with materialdried with magnesium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customthe residue was purified with silica gel column chromatography (EtOAc/hexane)

出典と根拠

ORDレコード
ord-3ee3a70c3ff240c28983933295f79340
出典データセット
uspto-grants-2002_02
特許番号
US06350749B1

反応ノート

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