Ethanol → Ethyl 2-Chloro-6-methylisonicotinate

HRID 1737533Notes

Reaction equation

HRID 1737533 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[C:4]([CH3:11])[N:3]=1.[CH2:12](O)[CH3:13]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([O:10][CH2:12][CH3:13])=[O:9])[CH:5]=[C:4]([CH3:11])[N:3]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 1412092-Chloro-6-methylpyridine-4-carboxylic acid

Product 1

HCID 22625009Ethyl 2-Chloro-6-methylisonicotinateYield 86%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 2-chloro-6-methyl-4-pyridinecarboxylic acid (2 g, 12 mmol) in ethanol (100 ml) and concentrated sulphuric acid (10 ml) was heated at reflux for 2 hours. The volatiles were removed by evaporation and the residue was dissolved in methylene chloride. The solution was washed with a saturated aqueous sodium hydrogen carbonate solution and brine, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluting with ethyl acetate/petroleum ether (1/9) to give ethyl 2-chloro-6-methyl-4-pyridinecarboxylate (2 g, 86%).

Workup

  1. temperatureat reflux for 2 hours
  2. customThe volatiles were removed by evaporation
  3. dissolutionthe residue was dissolved in methylene chloride
  4. washThe solution was washed with a saturated aqueous sodium hydrogen carbonate solution and brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed by evaporation
  7. customThe residue was purified by column chromatography
  8. washeluting with ethyl acetate/petroleum ether (1/9)

Sources & evidence

ORD record
ord-ced60354183346beba2ac41ec9b0fe20
Source dataset
uspto-grants-1999_10
Patent number
US05962458

Reaction notes

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