Highly selective hydrogenation of 2-chloro-5-cyanopyridine with an improved sponge nickel catalyst

Article abstract of DOI:10.1016/S0040-4039(99)01097-7

A practical synthesis of (6-chloropyridin-3-yl)methylamine (1), a key intermediate of neo-nicotinoide insecticides 2, was achieved by highly selective hydrogenation of 2-chloro-5-cyanopyridine (3). The hydrogenation of 3 with an improved Sponge nickel catalyst, prepared from an alloy of low nickel content (Ni 38%, Al 62%) and subjected to heat treatment in water, was carried out at 50°C and 1.2-1.4 kg/cm² hydrogen pressure to give 1 in 86% yield and (pyridin-3-yl)methylamine (4), a dechlorinated by-product, in only 2% yield.