Thionyl Chloride → 2,6-Dimethyl 4-chloropyridine-2,6-dicarboxylate

HRID 1740942

Reaktionsgleichung

Reaktionsgleichung von HRID 1740942
S(Cl)(Cl)=O.[CH3:5][O:6][C:7](=[O:16])[C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[C:10](Cl)[N:9]=1>>[Cl:14][C:12]1[CH:13]=[C:8]([C:7]([O:6][CH3:5])=[O:16])[N:9]=[C:10]([C:7]([O:6][CH3:5])=[O:16])[CH:11]=1

Komponenten

3

Edukt 2

HCID 24386Thionyl ChlorideHCID 18922464Methyl 4,6-dichloropyridine-2-carboxylate

Produkt 1

HCID 2378452,6-Dimethyl 4-chloropyridine-2,6-dicarboxylate

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

N-Ethyl-4-pyridone-2,6-dicarboxylic acid, prepared in Step A of Example 36, was treated with thionyl chloride and heated at 80° C. as described in the literature. The excess thionyl chloride was removed under reduced pressure and the remaining residue was cooled to 0° C. The product was slowly poured into cold methanol with vigorous stirring. The solvent was then removed in vacuo and the crude product was purified by silica gel column chromatography. Two products were isolated: the higher Rf product was 4,6-dichloropicolinic acid methyl ester while the lower Rf product was the title compound.

Aufarbeitung

  1. customThe excess thionyl chloride was removed under reduced pressure
  2. temperaturethe remaining residue was cooled to 0° C
  3. additionThe product was slowly poured into cold methanol with vigorous stirring
  4. customThe solvent was then removed in vacuo
  5. customthe crude product was purified by silica gel column chromatography
  6. customTwo products were isolated

Quellen und Nachweise

ORD-Eintrag
ord-5df0936f1d814e19b61d9d9b3a76914c
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05972975

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