Cyclobutanecarboxylic acid → 3,6-Dichloro-4-cyclobutylpyridazine

Participants

Reaction Conditions

Reaction Steps

3,6-Dichloropyridazine (10 g) was suspended in water (200 ml) and H2SO4 (19.7 g), cyclobutane carboxylic acid (32.7 g) was added and the reaction degassed under N2 at 70° C. Silver nitrate (2.28 g) was added followed by dropwise addition of ammonium persulfate (45.9 g) in water (120 ml). After an additional 1 h heating at 70° C., the reaction was poured onto ice, basified to pH 8-9 with aqueous ammonium hydroxide and extracted into ethyl acetate (3×500 ml), dried (MgSO4) and evaporated to dryness. Purified with hexane-ethyl acetate mixtures to obtain pure product (13.4 g). 1NMR (360 MHz, CDCl3) δ1.57 (2H, m), 1.82 (4H, m), 2.20 (1H, m), 3.30 (1H, m), 7.38 (1H, s); MS (ES+) m/e 217 [MH]+.

Provenance & Evidence