Ethanol → Ethyl chloronicotinate

HRID 1655579Notes

Reaction equation

HRID 1655579 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 chloronicotinate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-Chloropyridine-3-carboxylic acid (25 g) was refluxed 3 hours in 200 mL of benzene containing 150 mL of thionyl chloride. The reaction mixture was concentrated in vacuo and chased with toluene. The residue obtained was treated with 100 mL of ethanol and refluxed an additional 20 minutes. The ethanol was removed under reduced pressure and the product was dissolved in toluene. The toluene solution was dried over magnesium sulfate and concentrated in vacuo to give the product as a colorless oil which was used without further purification in the next step.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo and chased with toluene
  2. customThe residue obtained
  3. temperaturerefluxed an additional 20 minutes
  4. customThe ethanol was removed under reduced pressure
  5. dissolutionthe product was dissolved in toluene
  6. dry with materialThe toluene solution was dried over magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-baeb2dc6701c4cc4aa25ce7e6498444c
Source dataset
uspto-grants-1993_10
Patent number
US05250548

Reaction notes

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