Oxalyl chloride → 6-Methyl-2-(trifluoromethyl)-3-pyridinecarbonyl chloride

HRID 2300030Notes

Reaction equation

HRID 2300030 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([C:12]([OH:14])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:18])=O>ClCCl.CN(C)C=O>[CH3:1][C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([C:12]([Cl:18])=[O:14])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 183742876-Methyl-2-(trifluoromethyl)-3-pyridinecarboxylic acid

Product 1

HCID 183742676-Methyl-2-(trifluoromethyl)-3-pyridinecarbonyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.45 g of 6-methyl-2-trifluoromethylpyridin-3-ylcarboxyi ic acid in 20 ml of dichloromethane is charged initially, 3 drops of dimethylformamid c are added and the mixture is subsequently treated with 1.6 ml of oxalyl chloride. After the intensive evolution of gas has ceased, the mixture is kept at a bath temperature of 40° C. for another 1.5 hours and then evaporated. The crude product (0.56 g) that remains as residue can be directly reacted further. 1H NMR (CDCl3, ppm): 8.20 (1H,d); 7.51 (1H,d); 2.65 (3H, s).

Workup

  1. customthe mixture is kept at a bath
  2. customevaporated
  3. customcan be directly reacted further

Sources & evidence

ORD record
ord-23062f522e4248d8b60919172141aa2d
Source dataset
uspto-grants-2002_12
Patent number
US06498125B2

Reaction notes

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