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

HRID 2081994Notes

Reaction equation

HRID 2081994 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-4a627bd1d4b34b418a258b7a82dd644d
Source dataset
uspto-grants-1993_02
Patent number
US05187158

Reaction notes

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