Methanol → 6-Butyl-4-methoxycarbonyl-2-oxo-1,2-dihydropyridine

HRID 234760Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 234760
S(Cl)(Cl)=O.[CH2:5]([C:9]1[NH:10][C:11](=[O:18])[CH:12]=[C:13]([CH:17]=1)[C:14]([OH:16])=[O:15])[CH2:6][CH2:7][CH3:8].[CH3:19]O>>[CH2:5]([C:9]1[NH:10][C:11](=[O:18])[CH:12]=[C:13]([C:14]([O:16][CH3:19])=[O:15])[CH:17]=1)[CH2:6][CH2:7][CH3:8]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 540903426-Butyl-2-oxo-1,2-dihydro-isonicotinic acid

Produkt 1

HCID 152251016-Butyl-4-methoxycarbonyl-2-oxo-1,2-dihydropyridine

Versuchsvorschrift

12.5 ml (0.17 mol) of thionyl chloride are added dropwise to a suspension of 29.25 g (0.15 mol) of 6-butyl-2-oxo-1,2-dihydro-isonicotinic acid in 200 ml of methanol, while cooling with ice, and the mixture is stirred overnight at room temperature. It is concentrated to dryness and the residue is chromatographed over 450 g of silica gel (230-400 mesh) using methylene chloride→methylene chloride/methanol 10:1. Colourless crystals of melting point 106° C. crystallise from methylene chloride, ether and petroleum ether.

Aufarbeitung

  1. temperaturewhile cooling with ice
  2. concentrationIt is concentrated to dryness
  3. customthe residue is chromatographed over 450 g of silica gel (230-400 mesh)
  4. customColourless crystals of melting point 106° C. crystallise from methylene chloride, ether and petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-caceb24978cb4cbc9279bf0a7731c694
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05596006

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