Thionyl Chloride → 3-Chloroisonicotinoyl chloride hydrochloride

HRID 2067183Notes

Reaction equation

HRID 2067183 reaction equation
[Cl:1][C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:13])=O>C1(C)C=CC=CC=1>[ClH:1].[Cl:1][C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([Cl:13])=[O:5]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 27358163-Chloropyridine-4-carboxylic acid

Product 1

HCID 866418943-Chloroisonicotinoyl chloride hydrochloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 3-chloroisonicotinic acid (750 mg, 4.76 mmol, 1.0 eq) in 25 mL of toluene was added thionyl chloride (3.0 mL, 41.6 mmol, 8.7 eq) at room temperature. The reaction mixture was stirred at 100° C. for 3 hours. The mixture was concentrated under reduced pressure, dissolved in 25 mL of toluene and concentrated again to give crude 3-chloroisonicotinoyl chloride hydrochloride salt, which was used in the next step without further purification.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutiondissolved in 25 mL of toluene
  3. concentrationconcentrated again

Sources & evidence

ORD record
ord-a2dcbbe64fab4a199e4686f9206545c4
Source dataset
uspto-grants-2012_10
Patent number
US08293769B2

Reaction notes

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