1-(2-Pyridyl) amino-3-o-tolyloxy-2-propanolの合成

抄録

1-(2-Pyridyl) amino-3-o-tolyloxy-2-propanol, synthesized to obtain an analgesic, was reported by Beasley and others as melting at 138°, the compound synthesized melted at 109-110°. Reaction of 1, 2-epoxy-3-o-tolyloxypropane and 2-aminopyridine in methanol-water mixture afforded a compound of m.p. 134.5-135.5o, which undergoes hydrolysis with alkali but the compound of m.p. 109-110° obtained by its reaction with sodium amide in anhyd. ether no longer undergoes hydrolysis. From these facts and from infrared spectral measurement of the two compounds, it was assumed that the former took the imine form and the latter, the amine form. Consequently, the compound reported by Beasley and others was probably a compound of the imine form, i.e. α-o-tolyloxymethyl-2-imino-1, 2-dihydro-1-pyridineethanol.