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

HRID 1056052

Reaktionsgleichung

Reaktionsgleichung von HRID 1056052
[Cl-].[Al+3].[Cl-].[Cl-].[Br:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][C:13](=[O:22])[CH:14]=[CH:15]C1C=CC=CC=1>ClC1C=CC=CC=1>[Br:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:7]=1[NH:12][C:13](=[O:22])[CH:14]=[CH:15]2

Komponenten

4

Edukt 2

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

Produkt 1

HCID 109330948-Bromo-1,2-dihydroquinolin-2-oneAusbeute 67,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7964ChlorobenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

Aluminum chloride (2.6 g, 19.92 mmol) was added to a solution of N-(2-bromophenyl)cinnamamide (1.0 g, 3.32 mmol) in chlorobenzene, and the resulting mixture was heated at 125° C. for 2 h. The reaction mixture was then cooled to 50° C. and treated with ice-cold water (25 mL) to provide a brown precipitate. The precipitate was collected by vacuum filtration and dried in vacuo, then triturated with EtOH to provide 8-bromoquinolin-2(1H)-one (0.5 g, 67% yield) as an off-white solid. m/z (ESI, +ve) 226.2 (M+H)+

Aufarbeitung

  1. temperatureThe reaction mixture was then cooled to 50° C.
  2. customto provide a brown precipitate
  3. filtrationThe precipitate was collected by vacuum filtration
  4. customdried in vacuo
  5. customtriturated with EtOH

Quellen und Nachweise

ORD-Eintrag
ord-70bde04703204b5fb871d7eb38a46c36
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394297B2

Verknüpfte Notizen

Wird geladen…