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

HRID 1719486Notes

Reaction equation

HRID 1719486 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-c8fd3f17961a4f7e96e25770a1c38d41
Source dataset
uspto-grants-1985_09
Patent number
US04540564

Reaction notes

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