Hydrochloric Acid → 5-(Aminomethyl)-2-chloropyridine

Hydrazine hydrate (2.00 ml, 0.04 mol) was added at ambient temperature (20° C.) to a solution of N-(6-chloro-3-pyridylmethyl) phthalimide (10.70 g, 0.039 mol) in ethanol (150 ml), and the resulting solution was heated under reflux for 4 hours before being cooled to ambient temperature (20° C.). 25% w/v aqueous hydrochloric acid (60 ml) was added directly and the resulting mixture was heated under reflux for 1 hour. The reaction mixture was then cooled to ambient temperature (20° C.), filtered and evaporated under reduced pressure. The resulting concentrated mixture was filtered and the filtrate was cooled, with ice/salt bath cooling, and solid potassium hydroxide was added with stirring until the mixture became basic. The reaction mixture was then extracted with diethylether (5×150 ml). The combined ether extracts were dried using magnesium sulphate and evaporated under reduced pressure to give the product, 6-chloro-3-pyridylmethylamine as a brown oil (5.07 g, 90.6%).