Reaction #792179

Reaction equation

1,1,1-Trifluoroacetone

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

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

→

product

Yield 66.0%

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

Yield 66.0%

Conditions

Workup

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

Procedure

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