Water → 6-[2-Nitro-4-(trifluoromethyl)phenoxy]quinoline-2-carbonitrile

HRID 446193

Reaktionsgleichung

Reaktionsgleichung von HRID 446193
[C:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([OH:13])[CH:9]=2)[N:4]=1)#[N:2].[Cl-].[N+:15]([C:18]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][CH:19]=1)([O-:17])=[O:16].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O.C(Cl)Cl>[C:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:13][C:19]3[CH:20]=[CH:21][C:22]([C:24]([F:27])([F:25])[F:26])=[CH:23][C:18]=3[N+:15]([O-:17])=[O:16])[CH:9]=2)[N:4]=1)#[N:2]

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 144295346-Hydroxyquinoline-2-carbonitrileHCID 666082642-Nitro-4-trifluoromethylbenzene chloride

Produkt 1

HCID 587976996-[2-Nitro-4-(trifluoromethyl)phenoxy]quinoline-2-carbonitrileAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

The mixture of 2-cyano-6-hydroxyquinoline (0.50 g, 2.94 mmol), 2-nitro-4-trifluoromethylbenzene chloride (0.67 g, 2.94 mmol) and potassium carbonate (0.41 g, 2.97 mmol) in 30 ml of DMSO was heated to 100° C. for 30 min. Upon cooling to room temperature, the mixture was poured into 30 ml of cold water and exacted three times with methylene chloride. The combined organic layer was washed with water and dried over magnesium sulfate. The product was purified by flash chromatography using heptane/methylene chloride (1:2) as eluent in a yield of 35%.

Aufarbeitung

  1. temperatureUpon cooling to room temperature
  2. washThe combined organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customThe product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-72f8c18f7b4848229b893b2263e6f56f
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476450B2

Verknüpfte Notizen

Wird geladen…