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

HRID 343958Notes

Reaction equation

HRID 343958 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 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.

Workup

  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

Sources & evidence

ORD record
ord-4bf302890225462ab5b934f8ca89c93f
Source dataset
uspto-grants-1999_01
Patent number
US05863930

Reaction notes

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