Benzene, 1-fluoro-2-methyl-4-nitro- → 1-(2-Methyl-4-nitrophenyl)-3-(trifluoromethyl)pyridin-2(1H)-one

HRID 218511

Reaktionsgleichung

Reaktionsgleichung von HRID 218511
[F:1][C:2]([F:11])([F:10])[C:3]1[C:4](=[O:9])[NH:5][CH:6]=[CH:7][CH:8]=1.CC(C)([O-])C.[K+].F[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:20]=1[CH3:28]>CS(C)=O.O>[CH3:28][C:20]1[CH:21]=[C:22]([N+:25]([O-:27])=[O:26])[CH:23]=[CH:24][C:19]=1[N:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:10])[F:11])[C:4]1=[O:9]

Komponenten

6

Edukt 3

HCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-HCID 36784112(1H)-Pyridinone, 3-(trifluoromethyl)-HCID 23665647Potassium tert-butoxide

Produkt 1

HCID 595867011-(2-Methyl-4-nitrophenyl)-3-(trifluoromethyl)pyridin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2.5 g (15.3 mmol) of 3-(trifluoromethyl)pyridin-2(1H)-one are dissolved in 40 ml of dimethyl sulfoxide and admixed at room temperature with 2.58 g (22.9 mmol) of potassium tert-butoxide. The suspension is stirred at room temperature for 30 min, before 2.6 g (16.9 mmol) of 1-fluoro-2-methyl-4-nitrobenzene are added and the reaction solution is heated to 80° C. for 20 h. It is diluted cautiously with water. The solution is extracted repeatedly with dichloromethane. The combined organic extracts are washed with water and saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue is dissolved in acetonitrile and purified by preparative HPLC with a gradient of water and acetonitrile. The product fractions are combined and concentrated to dryness under reduced pressure. This affords 1.87 g (41% of theory) of the desired product.

Aufarbeitung

  1. additionare added
  2. extractionThe solution is extracted repeatedly with dichloromethane
  3. washThe combined organic extracts are washed with water and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue is dissolved in acetonitrile
  8. custompurified by preparative HPLC with a gradient of water and acetonitrile
  9. concentrationconcentrated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-aa728b67579c4200925a08884f0fba41
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198267B2

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