Hydrazine → 1-(3-Chloro-5-(4-chlorophenyl)pyridazin-4-yl)hydrazine

Participants

Reaction Conditions

Reaction Steps

To a stirring suspension of 3,4-dichloro-5-(4-chlorophenyl)pyridazine (2.58 g, 10 mmol) in 2-BuOH (150 mL) at RT was added anhydrous hydrazine (4.80 g, 150 mmol). The reaction mixture was heated at 60° C. under argon. HPLC/MS analysis indicated that the reaction was complete after 5 h. The reaction mixture was cooled to 0° C., and the product was collected by filtration. The solid was then washed with ice-cold 2-propanol (10 mL×2). After drying the solid under vacuum at room temperature for 16 h, the title compound, 1-(4-chloro-5-(4-chlorophenyl)pyridazin-3-yl)hydrazine was obtained in a 1.6:1 ratio with undesired 1-(3-chloro-5-(4-chlorophenyl)pyridazin-4-yl)hydrazine (2.16 g gross). 1-(4-chloro-5-(4-chlorophenyl)pyridazin-3-yl)hydrazine MS [M+H]+ 255; HPLC retention time=1.63 min. 1-(3-chloro-5-(4-chlorophenyl)pyridazin-4-yl)hydrazine MS [M+H]+ 255; HPLC retention time=1.09 min.

Provenance & Evidence