Dimethylformamide → 4-Benzoylpyridine

HRID 848722Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 848722
[N:1]1[CH:6]=[CH:5][C:4]([C:7](=NO)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.[H-].[Na+].[H][H].ClCC#N.CN(C)C=[O:27]>>[N:1]1[CH:6]=[CH:5][C:4]([C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:27])=[CH:3][CH:2]=1

Komponenten

6

Edukt 5

HCID 6228DimethylformamideHCID 7856ChloroacetonitrileHCID 24758Sodium hydrideHCID 542817HCID 542817, VerbindungHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 267314-Benzoylpyridine

Versuchsvorschrift

Phenyl 4-pyridinyl ketone oxime (5.4 g) was stirred in 50 ml of dimethyl formamide containing 1.5 g of a 50% dispersion of sodium hydride in oil, for 0.5 hours at room temperature. After the hydrogen evolution was completed, chloroacetonitrile (2.5 g) was added. The reaction mixture was stirred for 1 hour. The greater part of the dimethyl formamide was evaporated at reduced pressure, and then the residue was treated with ether and water. The ether layer was separated and dried over magnesium sulphate. The product was recrystallized from a mixture of ether and petroleum ether (40°-60° C.), yielding pure phenyl 4-pyridinyl ketone, O-cyanomethyl oxime (4.9 g, m.p. 101.5°-103° C.).

Aufarbeitung

  1. customThe greater part of the dimethyl formamide was evaporated at reduced pressure
  2. additionthe residue was treated with ether and water
  3. customThe ether layer was separated
  4. dry with materialdried over magnesium sulphate
  5. customThe product was recrystallized from a mixture of ether and petroleum ether (40°-60° C.)

Quellen und Nachweise

ORD-Eintrag
ord-0535ed77840846afb0b087c1cad702d7
Quelldatensatz
uspto-grants-1981_10
Patentnummer
US04297359

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