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

HRID 1606893Notes

Reaction equation

HRID 1606893 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-ed2534dba6a14381aecfa66e44859e1c
Source dataset
uspto-grants-1989_09
Patent number
US04863911

Reaction notes

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