1-(2-Chloro-8-fluoroquinolin-3-yl)ethanol → HCID 57707761, Verbindung

HRID 1019787Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1019787
[Cl:1][C:2]1[C:11]([CH:12]([OH:14])[CH3:13])=[CH:10][C:9]2[C:4](=[C:5]([F:15])[CH:6]=[CH:7][CH:8]=2)[N:3]=1>[O-2].[O-2].[Mn+4].C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:11]([C:12](=[O:14])[CH3:13])=[CH:10][C:9]2[C:4](=[C:5]([F:15])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Komponenten

4

Edukt 1

HCID 577079711-(2-Chloro-8-fluoroquinolin-3-yl)ethanol

Produkt 1

HCID 57707761HCID 57707761, VerbindungAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a round-bottomed flask containing toluene (183 mL) was added 1-(2-chloro-8-fluoroquinolin-3-yl)ethanol (6.20 g, 27.5 mmol) and manganese dioxide (19.1 g, 220 mmol, 8 eq). The reaction was heated to reflux for 2 h, cooled to rt, filtered and concentrated. The product was diluted with hexanes and filtered to give as a white solid 1-(2-chloro-8-fluoroquinolin-3-yl)ethanone (4.43 g, 72% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.40 (d, J=1.6 Hz, 1H), 7.71 (br d, J=8.2 Hz, 1H), 7.56 (td, J=7.8, 5.1 Hz, 1H), 7.54 (ddd, J=9.8, 7.8, 1.6 Hz, 1H). Mass Spectrum (ESI) m/e=223.9 (M+1).

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2 h
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additionThe product was diluted with hexanes
  6. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-7185985600ea4d58848dce9bf708f12f
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716290B2

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