Reaction #1116

Reaction equation

sodium bicarbonate

3,4-dichloro-2-ethylpyridine

4-(2,4-dichlorobenzylidene)cyclohexylamine

ammonium chloride

→

3-Chloro-4-[4-(2,4-dichlorobenzylidene)cyclohexyl]amino-2-ethylpyridine

Yield 7.0%

Solvents

N-methylpyrrolidone

Conditions

Workup

1. 1
   TemperatureAfter cooling
2. 2
   Extractionextracted with ethyl acetate
3. 3
   OtherThe product is purified by chromatography on silica gel

Procedure

1.6 g of 3,4-dichloro-2-ethylpyridine and 2.5 g of 4-(2,4-dichlorobenzylidene)cyclohexylamine are heated at 180° C. for 3.5 hours together with 55 g of ammonium chloride in 9 ml of N-methylpyrrolidone. After cooling, the mixture is poured into saturated sodium bicarbonate solution and extracted with ethyl acetate. The product is purified by chromatography on silica gel using ethyl acetate/heptane 1:4. Yield: 7%

Source