Acetic Acid → 5-(6-Chloro-3-methylimidazo[1,2-b]pyridazin-2-yl)-2-methylaniline

Participants

Reaction Conditions

Reaction Steps

To a mixture of 6-chloro-3-methyl-2-(4-methyl-3-nitrophenyl)imidazo[1,2-b]pyridazine (2.00 g, 6.60 mmol) in ethanol (100 mL) and water (25 mL) containing AcOH (39.6 mmol) is added iron (1.84 g, 33.0 mmol). The mixture is heated at 80° C. for 6 hours, then cooled, concentrated under reduced pressure and sat. aqueous NaHCO3 (100 mL) is added. The mixture is extracted with EtOAc (3×50 mL). Organic layer is collected, dried over Na2SO4, filtered and concentrated to dryness. The crude is purified via chromatography (hexanes to EtOAc) to afford the title compound (1.45 g, 80%) as a yellow solid: Rf 0.52 (EtOAc); LCMS (m/z)=273.3, 275.3 [M+H]+, tR=1.79 min.

Provenance & Evidence