Réaction #792179

Équation de réaction

1,1,1-Trifluoroacetone

3-chloro-2(1H)-pyridinone hydrazone

(3-chloro-pyridin-2-yl)-hydrazine

→

product

Rendement 66.0%

3-chloro-2(1H)-pyridinone (2,2,2-trifluoro-1-methylethylidene)hydrazone

Rendement 66.0%

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONAfter the addition
2. 2
   AutreThe solvent was removed under reduced pressure
3. 3
   Autrethe mixture partitioned between ethyl acetate (100 mL) and saturated aqueous sodium carbonate solution (100 mL)
4. 4
   AutreThe organic layer was dried
5. 5
   Autreevaporated
6. 6
   AutreChromatography on silica gel (eluted with ethyl acetate) gave

Mode opératoire

1,1,1-Trifluoroacetone (7.80 g, 69.6 mmol) was added to 3-chloro-2(1H)-pyridinone hydrazone (alternatively named (3-chloro-pyridin-2-yl)-hydrazine) (10 g, 69.7 mmol) at 20-25° C. After the addition was complete, the mixture was stirred for about 10 minutes. The solvent was removed under reduced pressure and the mixture partitioned between ethyl acetate (100 mL) and saturated aqueous sodium carbonate solution (100 mL). The organic layer was dried and evaporated. Chromatography on silica gel (eluted with ethyl acetate) gave the product as an off-white solid (11 g, 66% yield), m.p. 64-64.5° C. (after crystallization from ethyl acetate/hexanes).

Source