N-(2-Bromophenyl)cinnamamide → 8-Bromo-1,2-dihydroquinolin-2-one

HRID 1095667

Reaktionsgleichung

Reaktionsgleichung von HRID 1095667
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:18])[CH:10]=[CH:11]C1C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClC1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[NH:8][C:9](=[O:18])[CH:10]=[CH:11]2

Komponenten

4

Edukt 2

HCID 764332N-(2-Bromophenyl)cinnamamideHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 109330948-Bromo-1,2-dihydroquinolin-2-oneAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7964ChlorobenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of N-(2-bromophenyl)cinnamamide (172.3 g, 570.3 mmol), aluminum chloride (456 g, 342 mmol) and chlorobenzene (1000 ml) were allowed to stir at 100° C. for 7 hours followed by cooling to ambient temperature overnight. The resulting mixture was poured onto 2 kg of ice and was allowed to warm to ambient temperature over 1 hour. The resulting mixture was extracted with dichloromethane. The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The resulting solids were triturated with 1000 ml hexanes. The solids were vacuum dried to yield title compound. (83 g, 65% yield) MS ESI (+) m/z 224 and 226 (M+1 of each isotope) detected.

Aufarbeitung

  1. temperatureby cooling to ambient temperature overnight
  2. temperatureto warm to ambient temperature over 1 hour
  3. extractionThe resulting mixture was extracted with dichloromethane
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting solids were triturated with 1000 ml hexanes
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-b6c5860b1e9b4a00b921c599e6b0883c
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138181B2

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