3-chloro-N-(2-fluorophenyl)propanamide → 8-Fluoro-1,2,3,4-tetrahydroquinolin-2-one

HRID 1521628Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1521628
[Cl-].[Al+3].[Cl-].[Cl-].Cl[CH2:6][CH2:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17])=[O:9]>>[F:17][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[NH:10][C:8](=[O:9])[CH2:7][CH2:6]2

Komponenten

3

Edukt 2

HCID 42560293-chloro-N-(2-fluorophenyl)propanamideHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 151448738-Fluoro-1,2,3,4-tetrahydroquinolin-2-one

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a stirred aluminum chloride (26.53 g, 0.199 mol) was added 3-chloro-N-(2-fluorophenyl) propanamide (109-1; 10.0 g, 0.0497 mol). Reaction mass was heated 120° C. and stirred for 5 h. Then reaction mixture was cooled to room temperature and diluted with ice cold water (200 mL) and washed with 17% aqueous hydrochloric acid solution (50 mL) slowly under cooling condition and extracted with ethyl acetate (4×100 mL). The combined organic layer was washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated under vacuum to afford the crude compound which was purified by silica gel column chromatography to obtain the title compound. MS (M+1): 166.1.

Aufarbeitung

  1. customReaction mass
  2. customThen reaction mixture
  3. temperaturewas cooled to room temperature
  4. washwashed with 17% aqueous hydrochloric acid solution (50 mL) slowly
  5. temperatureunder cooling condition
  6. extractionextracted with ethyl acetate (4×100 mL)
  7. washThe combined organic layer was washed with saturated aqueous sodium chloride solution
  8. dry with materialdried over sodium sulphate
  9. concentrationconcentrated under vacuum
  10. customto afford the crude compound which
  11. customwas purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-087ea4228fc2457599f2f6642d1d5749
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073929B2

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