Thionyl Chloride → 3-Chloropyridine-2-carbonyl chloride

HRID 1497693

Reaction equation

HRID 1497693 reaction equation
[Cl:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[CH:6][CH:7]=1.S(Cl)([Cl:13])=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([C:8]([Cl:13])=[O:10])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 8246323-Chloropyridine-2-carboxylic acid

Product 1

HCID 450814973-Chloropyridine-2-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a suspension of 3-chloropicolinic acid (1.58 g, 10 mmol) in toluene (6 mL) was added an excess of thionyl chloride (9.52 g, 5.84 mL, 80.0 mmol) at room temperature under a nitrogen atmosphere. The resulting suspension was heated to 120° C. (oil bath temperature) and stirred for 20 h. Then, the solvent and excess of thionyl chloride were removed under vacuum and the residue was dissolved one more time in toluene and the solvent was removed again. The resulting residue was dried under high vacuum and used in the next step.

Workup

  1. customThen, the solvent and excess of thionyl chloride were removed under vacuum
  2. dissolutionthe residue was dissolved one more time in toluene
  3. customthe solvent was removed again
  4. customThe resulting residue was dried under high vacuum

Sources & evidence

ORD record
ord-0c111a772a66422795d657a647f2ebe2
Source dataset
uspto-grants-2015_12
Patent number
US09199987B2

Linked notes

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