Benzene → 3-Benzoyl-2-chloropyridine

HRID 65524

Reaktionsgleichung

Reaktionsgleichung von HRID 65524
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[Al+3].[Cl-].[Cl-].[Cl-].O.[CH:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[C:4]([C:3]1[C:2]([Cl:1])=[N:10][CH:9]=[CH:8][CH:7]=1)(=[O:5])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

5

Edukt 4

HCID 241BenzeneHCID 962WaterHCID 27745412-Chloronicotinoyl chlorideHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 8246193-Benzoyl-2-chloropyridine

Versuchsvorschrift

To a cooled solution of 150 g 2-chloro-nicotinoyl chloride in 400 ml benzene there is added slowly 238 g AlCl3. After refluxing 2 hrs. the reaction mixture is added with stirring to a slightly acidic ice: water mixture. The organic layer is separated and the aqueous one is extracted with ethyl ether. The combined organic layers are washed with HONa 1N, then with water, and dried over Na2SO4. The excess benzene is distilled at water pump pressure in a rotary evaporator and the residual oil is distilled in vacuo. Yield: 157 g of title product, b.p. 123° C./0.05 mm; m.p. 35°-7° C.; UV (ethanol): λmax. 254 nm., ε: 17,180; Cl 15.97 (16.29).

Aufarbeitung

  1. temperatureAfter refluxing 2 hrs
  2. additionthe reaction mixture is added
  3. customThe organic layer is separated
  4. extractionthe aqueous one is extracted with ethyl ether
  5. washThe combined organic layers are washed with HONa 1N
  6. dry with materialwith water, and dried over Na2SO4
  7. distillationThe excess benzene is distilled at water pump pressure in a rotary evaporator
  8. distillationthe residual oil is distilled in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3dbd27525d1a4d5e83fb5b6af286c71b
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04614833

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