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

HRID 1638861Notes

Reaction equation

HRID 1638861 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-3b6b1a88bd5948f19eebc3a80c14d1f9
Source dataset
uspto-grants-1989_11
Patent number
US04880921

Reaction notes

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