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

HRID 1700502노트

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HRID 1700502 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8471Triethylamine용매

반응 조건

온도
220 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-7b1d9882db1e45fab35f7d280fdeb31f
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06350749B1

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