Tetrahydrofuran → 7-(4-Fluorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one

HRID 1700502ノート

反応式

HRID 1700502 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[CH2:11][C:10](=O)[CH2:9]2)=[CH:4][CH:3]=1.Cl.[NH2:17][CH2:18][C:19]#[C:20][CH3:21].O1CCCC1>C(N(CC)CC)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:9][C:10]3[N:17]=[CH:18][CH:19]=[C:20]([CH3:21])[C:11]=3[C:12](=[O:14])[CH2:13]2)=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 7301365-(4-Fluorophenyl)cyclohexane-1,3-dioneHCID 12599999But-2-yn-1-amine hydrochloride

生成物 1

HCID 183174737-(4-Fluorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one収率 28.9%

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

反応条件

温度
220 °C

実験手順

To a mixture of 5-(4-fluorophenyl)cyclohexane-1, 3-dione (0.98 g), 1-amino-2-butyne hydrochloride (0.5 g), molecular sieves 4A (2 g) and tetrahydrofuran (20 ml) was added triethylamine (0.48 g), and the mixture was refluxed for 14 hours and cooled. Insoluble materials were filtered off. Under reduced pressure, the solvent was evaporated, and the residue was stirred for 6 hours at 220° C. and cooled, to which were added ethyl acetate and sodium hydrogen carbonate solution. The organic layer 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 oil of 7-(4-fluorophenyl)-4methyl-5,6,7,8-tetrahydroquinolin-5-one (0.35 g).

後処理

  1. temperaturethe mixture was refluxed for 14 hours
  2. temperaturecooled
  3. filtrationInsoluble materials were filtered off
  4. customUnder reduced pressure, the solvent was evaporated
  5. temperaturecooled, to which
  6. additionwere added ethyl acetate and sodium hydrogen carbonate solution
  7. washThe organic layer was washed with water and saturated brine
  8. dry with materialdried with magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customthe residue was purified with silica gel column chromatography (EtoAc/hexane)

出典と根拠

ORDレコード
ord-7b1d9882db1e45fab35f7d280fdeb31f
出典データセット
uspto-grants-2002_02
特許番号
US06350749B1

反応ノート

読み込み中…