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

HRID 1708143Notes

Reaction equation

HRID 1708143 reaction equation
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]

Participants

4

Reactant 3

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

Product 1

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

Procedure

12.5 ml (0.17 mol) of thionyl chloride are added dropwise with ice-cooling 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 and the mixture is stirred overnight at room temperature. It is concentrated to dryness and the residue is chromatographed on 450 g of silica gel (230-400 mesh) using dichloromethane→dichloromethane/methanol 10:1. 29.6 g (94%) of colourless crystals m.p.: 106° C. crystallise from dichloromethane, ether and petroleum ether.

Workup

  1. concentrationIt is concentrated to dryness
  2. customthe residue is chromatographed on 450 g of silica gel (230-400 mesh)
  3. custom29.6 g (94%) of colourless crystals m.p.: 106° C. crystallise from dichloromethane, ether and petroleum ether

Sources & evidence

ORD record
ord-4c736443859649b485455c2695909a65
Source dataset
uspto-grants-1994_10
Patent number
US05356911

Reaction notes

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