Thionyl Chloride → 4-Chloronicotinoyl chloride hydrochloride
Reaction equation
[Cl:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]=[CH:4][CH:3]=1.S(Cl)([Cl:13])=O>C1(C)C=CC=CC=1>[ClH:1].[Cl:1][C:2]1[C:7]([C:8]([Cl:13])=[O:10])=[CH:6][N:5]=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a suspension of 4-chloronicotinic acid (1.57 g, 10.0 mmol, 1.0 eq) in 25 mL of toluene was added thionyl chloride (1.8 mL, 25.0 mmol, 2.5 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 4-chloronicotinoyl chloride hydrochloride salt, which was used in the next step without further purification.
Workup
- concentrationThe mixture was concentrated under reduced pressure
- dissolutiondissolved in 25 mL of toluene
- concentrationconcentrated again
Sources & evidence
- ORD record
- ord-4a099cf886524f4fbfb6559b6290c35c
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08710048B2
Reaction notes
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