Phosphorus oxychloride → 8-(Benzyloxy)-2-chloroquinoline

HRID 1777172Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1777172
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16](O)[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:22]>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([Cl:22])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 178515619HCID 178515619, Verbindung

Produkt 1

HCID 220422348-(Benzyloxy)-2-chloroquinolineAusbeute 85 %

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

8-(benzyloxy)quinolin-2-ol (6.6 g, 26.3 mmol) was dissolved in POCl3 (50 mL). The mixture was stirred at 90° C. for 16 h. The POCl3 was evaporated and to the residue was added EtOAc (100 mL) and the solution was washed with a.q. NaHCO3 (80 mL) and H2O (80 mL). The EtOAc was removed under vacuum to give the desired compound (6.0 g, yield 85%). LCMS (m/z): 270.1 [M+H]+

Aufarbeitung

  1. customThe POCl3 was evaporated and to the residue
  2. additionwas added EtOAc (100 mL)
  3. washthe solution was washed with a.q
  4. customThe EtOAc was removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-fb616de908884d78bb8380893a5ff4d4
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09266836B2

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