Aluminum(III) Chloride → HCID 67977265, Verbindung

HRID 2174472Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2174472
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:4][C:3]=1[NH:17][C:18](=[O:28])/[C:19](/[CH3:27])=[CH:20]/C1C=CC=CC=1.[Cl-].[Cl-].[Cl-].[Al+3]>ClC1C=CC=CC=1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)=[C:4]2[C:3]=1[NH:17][C:18](=[O:28])[C:19]([CH3:20])=[CH:27]2

Komponenten

5

Edukt 2

HCID 6451240Aluminum(III) ChlorideHCID 67974754HCID 67974754, Verbindung

Produkt 1

HCID 67977265HCID 67977265, VerbindungAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 7964ChlorobenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

(E)-N-(2-chloro-5-(2-(piperidin-1-yl)ethoxy)phenyl)-2-methyl-3-phenylacrylamide (100 mg, 0.2 mmol, 1 eq.) was placed in chlorobenzene (500 μL), in the presence of aluminium trichloride (201 mg, 1.5 mmol, 6 eq.). The reaction mixture was heated at 125° C. and stirred for 2 hours. After cooling down to room temperature, it was diluted with a water and ice mixture and extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel to afford 8-chloro-3-methyl-5-(2-(piperidin-1-yl)ethoxy)quinolin-2(1H)-one (25 mg, 31%).

Aufarbeitung

  1. temperatureAfter cooling down to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-7e8845ca6692476bb8cb247866728f07
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09061999B2

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