Oxalyl chloride → 3-Pyridinecarbonyl chloride, 6-(2,2,2-trifluoroethoxy)-

HRID 341477Notes

Reaction equation

HRID 341477 reaction equation
[F:1][C:2]([F:15])([F:14])[CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][N:6]=1.C(Cl)(=O)C([Cl:19])=O>ClCCCl>[F:1][C:2]([F:15])([F:14])[CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([Cl:19])=[O:10])=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 27810286-(2,2,2-Trifluoroethoxy)pyridine-3-carboxylic acid

Product 1

HCID 235127223-Pyridinecarbonyl chloride, 6-(2,2,2-trifluoroethoxy)-Yield 102%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To 6-(2,2,2-trifluoro-ethoxy)-nicotinic acid (100 mg, 0.45 mmol) was added DCE (5 mL) and oxalyl chloride (60 ul, 0.68 mmol) under an atmosphere of nitrogen. The mixture was stirred at rt for 1.5 h then heated at 80 C for 2 h and after cooling to room temperature, evaporated to give the title compound as a pale yellow oil (110 mg, 100%). Method C HPLC-MS (in MeOH, identifying the methyl ester): MH+ requires m/z=236. Found: m/z=236, Rt=1.41 min (95%).

Workup

  1. temperaturethen heated at 80 C for 2 h
  2. temperatureafter cooling to room temperature
  3. customevaporated

Sources & evidence

ORD record
ord-d3be77bdd860451bb68698dc436494ad
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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