Reacción #8601

Ecuación de reacción

sodium hydroxide

2-(4-chloro-2-pyridinyl)-1-(4-fluorophenyl)ethanone

hydroxylamine hydrochloride

→

2-(4chloro-2-pyridinyl)-1-(4-fluorophenyl)ethanone oxime

Rendimiento 84.0%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe resulting suspension was heated
2. 2
   Temperaturaat reflux for 2 hours
3. 3
   ConcentraciónThe mixture was concentrated
4. 4
   workup.ADDITIONwater was added to the resulting slurry
5. 5
   OtroA white precipitate formed
6. 6
   Filtraciónwhich was collected by filtration
7. 7
   Lavadowashed with water
8. 8
   Secadodried (magnesium sulfate)

Procedimiento

To a solution of 2-(4-chloro-2-pyridinyl)-1-(4-fluorophenyl)ethanone (9.6 g, 38 mmol) in methanol (200 mL) was added hydroxylamine hydrochloride (13.5 g, 190 mmol) followed by the addition of a sodium hydroxide solution (7.8 g, 190 mmol in 50 mL of water). The resulting suspension was heated at reflux for 2 hours and then allowed to cool to room temperature. The mixture was concentrated and water was added to the resulting slurry. A white precipitate formed, which was collected by filtration, washed with water and dried (magnesium sulfate) to give 2-(4chloro-2-pyridinyl)-1-(4-fluorophenyl)ethanone oxime (8.45 g, 84%) as a white solid. 1H-NMR (DMSO-d6): δ 11.56 (s, 1H), 8.44 (d, 1H), 7.80 (m, 2H), 7.40 (m, 2H), 7.22 (m, 2H), 4.29 (s, 2 H); 19F-NMR (DMSO-d6): δ −113.44; MS m/z 265 (M+1).

Fuente