6-(2-Benzylidenehydrazinyl)-3-chloro-4-(pyrrolidin-1-yl)pyridazine → 6-Chloro-3-phenyl-7-(1-pyrrolidinyl)-1,2,4-triazolo[4,3-b]pyridazine

Participants

Reaction Steps

A slurry of N-benzylidene-N′-[6-chloro-5-(pyrrolidin-1-yl)pyridazin-3-yl]hydrazine (14 g, 0.046 mol) and lead(IV) acetate (24 g, 0.055 mol) in acetic acid (300 ml) was stirred at 60° C. under nitrogen overnight. The solvent was removed in vacuo, and the residue was purified by flash chromatography on silica gel, eluting with 0-10% methanol in ethyl acetate. The title compound was isolated as a yellow solid (4.1 g, 30%). 1H NMR (250 MHz, CDCl3) δ2.05 (4H, m), 3.56 (4H, m), 7.05 (1H, s), 7.51 (3H, m), 8.42 (2H, m). MS (ES+) m/e 300 [MH]+, 302 [MH]+.

Provenance & Evidence