Dimethylformamide → 2-Chloro-5-(trifluoromethyl)pyridine-3-carbonyl chloride

HRID 2089244Notes

Reaction equation

HRID 2089244 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:3]=1[C:4](O)=[O:5].C(Cl)(=O)C([Cl:18])=O.CN(C=O)C>C(Cl)Cl>[Cl:1][C:2]1[N:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:3]=1[C:4]([Cl:18])=[O:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 121402272-Chloro-5-(trifluoromethyl)nicotinic acid

Product 1

HCID 378634602-Chloro-5-(trifluoromethyl)pyridine-3-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-chloro-5-(trifluoromethyl)nicotinic acid (1.147 g, 4.83 mmol) in DCM (20 mL) was added oxalyl chloride (630 L, 7.35 mmol) dropwise with stirring. A single drop of DMF was added and the reaction mixture was stirred 40° C. for 1 hour. Concentration of the reaction mixture in vacuo resulted in the title compound as a brown oil.

Workup

  1. stirringthe reaction mixture was stirred 40° C. for 1 hour

Sources & evidence

ORD record
ord-37f91c9a324049e7929dcaded6fe7233
Source dataset
uspto-grants-2013_05
Patent number
US08436023B2

Reaction notes

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