Ethanol → Ethyl chloronicotinate

HRID 843982Notes

Reaction equation

HRID 843982 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH2:15](O)[CH3:16]>>[CH2:15]([O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[N:10][C:2]=1[Cl:1])[CH3:16]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 762582-Chloronicotinic acid

Product 1

HCID 2796614Ethyl chloronicotinate

Procedure

To a solution 2-Chloro-nicotinic acid (12.5 g) in Ethanol (250 ml) was added thionyl chloride (5.77 ml) dropwise and refluxed for 1.5 hours. The mixture was concentrated to remove ethanol and diluted with 300 ml water. Solid sodium bicarbonate was added to adjust the solution to pH 8.0. This was extracted with ethyl acetate, washed with water, saturated bicarbonate solution, water and brine, dried over Na2SO4, filtered and concentrated to a yellow liquid (10.0 g). MW 185.61; MS (m/e) 185 (M+).

Workup

  1. temperaturerefluxed for 1.5 hours
  2. concentrationThe mixture was concentrated
  3. customto remove ethanol
  4. additiondiluted with 300 ml water
  5. additionSolid sodium bicarbonate was added
  6. extractionThis was extracted with ethyl acetate
  7. washwashed with water, saturated bicarbonate solution, water and brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated to a yellow liquid (10.0 g)

Sources & evidence

ORD record
ord-d27f9389f0474a039a597db7471fe4e0
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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