Nicotinic Acid → 3-Pyridinecarbonyl chloride, hydrochloride (1:1)

HRID 1199562Notes

Reaction equation

HRID 1199562 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.S(Cl)([Cl:12])=O>>[ClH:12].[C:1]([Cl:12])(=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

Participants

3

Reactant 2

HCID 938Nicotinic AcidHCID 24386Thionyl Chloride

Product 1

HCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)Yield 91%

Procedure

To nicotinic acid (41 g, 0.333 mol) at 0° C. was added thionyl chloride (115 ml, 1.58 mol) with stirring. The mixture was refluxed for one hour, and the white crystalline product was filtered and washed sparingly with dry benzene. Excess thionyl chloride was azeotroped off with dry benzene immediately before use. Yield 90% (53.97 g) of nicotinoyl chloride hydrochloride; NMR, IR identical with literature values.

Workup

  1. temperatureThe mixture was refluxed for one hour
  2. filtrationthe white crystalline product was filtered
  3. washwashed sparingly with dry benzene
  4. customExcess thionyl chloride was azeotroped off with dry benzene immediately before use

Sources & evidence

ORD record
ord-196d22dbdbce4a96a4eec412837fe2e3
Source dataset
uspto-grants-1990_02
Patent number
US04900837

Reaction notes

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