Aluminum(III) Chloride → 6-Bromo-8-chloro-3,4-dihydroquinolin-2(1H)-one

HRID 530335

Reaktionsgleichung

Reaktionsgleichung von HRID 530335
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:13])[CH2:10][CH2:11]Cl)=[C:4]([Cl:14])[CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-]>>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[C:4]([Cl:14])[CH:3]=1)[NH:8][C:9](=[O:13])[CH2:10][CH2:11]2

Komponenten

3

Edukt 2

HCID 6451240Aluminum(III) ChlorideHCID 43346898N-(4-bromo-2-chlorophenyl)-3-chloropropanamide

Produkt 1

HCID 709797726-Bromo-8-chloro-3,4-dihydroquinolin-2(1H)-oneAusbeute 27 %

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A flame-dried 500-mL flask equipped with a magnetic stirring bar was charged with N-(4-bromo-2-chloro-phenyl)-3-chloro-propionamide (29.7 g, 0.1 mol) and aluminium chloride (53.3 g, 0.4 mol). In a pre-heated oil bath, the flask was heated at 140° C. for 1 hr. After cooling to room temperature, the mixture was treated with ice-water slowly and extracted with EtOAc. The organic layer was washed with water and brine in sequence, dried over anhy. Na2SO4, filtered, and concentrated in vacuo. The resulting residue was then purified by flash chromatography (silica gel, 30% ethyl acetate in hexane) to afford the title compound (7.0 g, 27% yield) as a white solid.

Aufarbeitung

  1. customA flame-dried 500-mL flask equipped with a magnetic stirring bar
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water and brine in sequence
  5. customdried over anhy
  6. filtrationNa2SO4, filtered
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was then purified by flash chromatography (silica gel, 30% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-c48d1d1d9f234c3f86708cceda9c58a1
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353081B2

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