Ethanol → Ethyl 2-chloroisonicotinate

HRID 899982Notes

Reaction equation

HRID 899982 reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[CH:10]=[CH:9][N:8]=1.[CH2:16](O)[CH3:17]>O>[Cl:6][C:7]1[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:10]=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 2369852-Chloroisonicotinic acid

Product 1

HCID 2762942Ethyl 2-chloroisonicotinate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1 ml of concentrated sulfuric acid is added to a solution of 2.2 g of 2-chloropyridine-4-carboxylic acid in 30 ml of ethanol. The reaction mixture is refluxed with stirring for 16 hours and then concentrated to dryness under reduced pressure. The residue thus obtained is taken up in 30 ml of water and then extracted with 3×30 ml of dichloromethane. The organic phase is dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure. The oil thus obtained is purified by filtration through 13 g of silica, eluting with dichloromethane. The fractions containing the expected product are concentrated to dryness under reduced pressure. 2.1 g of ethyl 2-chloropyridine-4-carboxylate are thus obtained.

Workup

  1. temperatureThe reaction mixture is refluxed
  2. concentrationconcentrated to dryness under reduced pressure
  3. customThe residue thus obtained
  4. extractionextracted with 3×30 ml of dichloromethane
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe oil thus obtained
  9. filtrationis purified by filtration through 13 g of silica
  10. washeluting with dichloromethane
  11. additionThe fractions containing the expected product
  12. concentrationare concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-053846434bff422789c9aa1601082348
Source dataset
uspto-grants-2008_04
Patent number
US07354933B2

Reaction notes

Loading…