Oxalyl chloride → 2-(4-Trifluoromethyl-phenyl)-nicotinoyl chloride

HRID 1531281Notes

Reaction equation

HRID 1531281 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][C:5]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1.O[Li].O.[Li].C(Cl)(=O)C([Cl:28])=O>C(Cl)Cl.CN(C=O)C.O.C1COCC1>[F:17][C:16]([F:19])([F:18])[C:13]1[CH:14]=[CH:15][C:10]([C:5]2[N:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([Cl:28])=[O:2])=[CH:11][CH:12]=1

Participants

9

Reactant 4

HCID 65578Oxalyl chlorideHCID 168937Lithium hydroxide, monohydrateHCID 3028194LithiumHCID 539509912-(4-Trifluoromethyl-phenyl)-nicotinic acid methyl ester

Product 1

HCID 212533632-(4-Trifluoromethyl-phenyl)-nicotinoyl chloride

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the title B compound, 2-(4-trifluoromethyl-phenyl)-nicotinic acid methyl ester (0.626 g, 2.228 mmol) in 1:1 THF:H2O (10 mL) is added LiOH.H2O (0.187 g, 4.456 mmol). After 3.5 h, the reaction mixture is concentrated to dryness under reduced pressure. To a slurry of the crude lithium salt in methylene chloride (10 mL) is added oxalyl chloride (0.78 mL, 8.91 mmol) followed by a few drops DMF. After stirring 16 h, the reaction mixture is concentrated to dryness under reduced pressure and used as is without purification.

Workup

  1. concentrationthe reaction mixture is concentrated to dryness under reduced pressure
  2. concentrationthe reaction mixture is concentrated to dryness under reduced pressure
  3. customas is without purification

Sources & evidence

ORD record
ord-a9c82025090045d295f54f6006b424bb
Source dataset
uspto-grants-2001_03
Patent number
US06197798B1

Reaction notes

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