Pyridine → HCID 13127539, compound

Participants

Reaction Steps

Acetyl chloride (34 ml) was added to a stirred suspension of 5-amino-1-(2-chloro-4-methylphenyl)-4-cyanopyrazole (8.0 g) in chloroform (34 ml) at 0° C. A solution of pyridine (5.4 ml) in chloroform (34 ml) was then added to the suspension thus obtained over 10 minutes, with stirring at 0° C. to 2° C. maintained by external cooling. The reaction mixture was then stirred at laboratory temperature for 2.5 hours and the solution thus obtained was evaporated to dryness. The residue was dissolved in ethanol (100 ml) and basified with aqueous ammonia (d: 0.880). The basified solution was heated at reflux for 10 minutes and then evaporated to dryness. The residue was dissolved in dichloromethane (500 ml) and water (500 ml) and the organic layer was separated, washed successively once with water, twice with 2N hydrochloric acid and twice with water, dried over anhydrous magnesium sulphate and evaporated. The colourless solid thus obtained was crystallised from toluene (30 ml) to give 5-acetamido-1-(2-chloro-4-methylphenyl)-4-cyanopyrazole (6.54 g), m.p. 146°-147° C., in the form of colourless crystals.

Provenance & Evidence