Pyridine → 3-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazole-4-carbonitrile

Participants

Reaction Conditions

Reaction Steps

Add a solution of 0.25 g of 4-amino-3-(5-nitro-2-furyl)-1-phenylpyrazole hydrochloride in 2 ml of pyridine dropwise over a period of from 1 to 2 hours to a solution of 0.22 g of sodium nitrite in 3 ml of concentrated sulfuric acid and 1.75 ml of water at 0° C. Stir the resulting reaction mixture for 0.5 hour, and then precipitate the diazonium salt by adding ice and water to the reaction mixture. Add the precipitate to a heated (90° C) solution of 300 mg of potassium cyanide and 200 ml of copper(I)cyanide in 20 ml of water. Stir the prepared admixture for 15 minutes at 90° C, cool down, draw off the formed precipitate and chromatograph with methylene chloride on silica gel to obtain 3-(5-nitro-2-furyl)-1-phenylpyrazole-4-carbonitrile [m.p. 190° to 192° C].

Provenance & Evidence