Hydrazine → Pyridine, 2,3,5-trichloro-

Participants

Reaction Conditions

Reaction Steps

A mixture was prepared containing 50.3 grams (0.2 mole) of pentachloropyridine, 20 grams (0.24 mole) of sodium bicarbonate and 6.9 grams (0.205 mole) of 95 percent hydrazine in 215 milliliters of propylene glycol methyl ether. The mixture was heated at 92° C., with stirring, for 1.5 hours. The mixture was cooled to 30° C. and 50 milliliters of propylene glycol methyl ether was added. To this mixture was added 350 milliliters of a 10 percent sodium hypochlorite solution, over a 20 minute period while the temperature of the solution was maintained at 45°-50° C. At the completion of the reaction, the solution was diluted with 100 milliliters of water and extracted with hexane. The hexane extract was washed with water and the hexane evaporated off. The oily product which remained was dissolved in 250 milliliters of propylene glycol methyl ether and 20 grams of sodium bicarbonate and 6.9 grams of 95 percent hydrazine were added thereto. The mixture was heated at 92° C. for 1.5 hours and 1.0 gram of 95 percent hydrazine was added. Heating was continued for 3 additional hours and the reaction mixture was cooled to 45° C. To this mixture was added 450 milliliters of a 10 percent sodium hypochlorite solution over a 20 minute period while maintaining the reaction temperature at 45°-50° C. The reaction mixture was extracted with hexane and the hexane extract was washed with water and the hexane was removed by evaporation. The crude 2,3,5-trichloropyridine product was obtained in a yield of 30.5 grams and found to be 94.6 percent pure.

Provenance & Evidence