Reacción #157988

Ecuación de reacción

N-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,6-dimethylpheyl]quinoline-6-carboxamide-1-oxide

phosphorus oxychloride

potassium carbonate

→

4-chloro-N-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,6-dimethylphenyl]quinoline-6-carboxamide

Rendimiento 23.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted twice with ethyl acetate
2. 2
   Lavadowashed with water
3. 3
   Secadodried over anhydrous magnesium sulfate
4. 4
   OtroThe drying agent (anhydrous magnesium sulfate) was removed by filtration
5. 5
   workup.DISTILLATIONthe solvent was distilled off under the reduced pressure
6. 6
   OtroThe residue was purified by column chromatography

Procedimiento

To crude product of N-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,6-dimethylpheyl]quinoline-6-carboxamide-1-oxide (97 mg), phosphorus oxychloride (3.0 g) was added and the mixture was stirred under heating at 100° C. for 1 hour. The reaction solution was poured into ice water, neutralized with potassium carbonate and extracted twice with ethyl acetate. The organic phases were combined and washed with water, and dried over anhydrous magnesium sulfate. The drying agent (anhydrous magnesium sulfate) was removed by filtration and the solvent was distilled off under the reduced pressure. The residue was purified by column chromatography to obtain 2-chloro-N-[4-(,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,6-dimethylphenyl]quinoline-6-carboxamide (35 mg, yield 35%) and 4-chloro-N-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,6-dimethylphenyl]quinoline-6-carboxamide (23 mg, yield 23%).

Fuente