Ethanol → Ethyl chloronicotinate

HRID 1440795Notes

Reaction equation

HRID 1440795 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.S(Cl)(Cl)=O.[CH2:15](O)[CH3:16]>C1C=CC=CC=1>[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:15][CH3:16])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 762582-Chloronicotinic acid

Product 1

HCID 2796614Ethyl chloronicotinateYield 90%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-Chloropyridine-3-carboxylic acid (7.9 g) and thionyl chloride (45 ml) were heated for 3 hours in benzene (65 ml) under reflux. The reaction mixture was concentrated to leave an oil, which was added dropwise to ethanol (40 ml). The mixture was heated for further one hour under reflux. The solvent was distilled, and the residue was dissolved in toluene. The solution was dried over anhydrous magnesium sulfate. The solvent was distilled to leave the title compound (8.4 g, 90%) as a pale yellow oil.

Workup

  1. temperatureunder reflux
  2. concentrationThe reaction mixture was concentrated
  3. customto leave an oil, which
  4. temperatureThe mixture was heated for further one hour
  5. temperatureunder reflux
  6. distillationThe solvent was distilled
  7. dissolutionthe residue was dissolved in toluene
  8. dry with materialThe solution was dried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled

Sources & evidence

ORD record
ord-16f2b6b9f37940deb19d3d6c490ef7cf
Source dataset
uspto-grants-1996_03
Patent number
US05500427

Reaction notes

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