Dimethylamine → 2-Dimethylaminomethyl-3-hydroxy-4-methylpyridine

Participants

Reaction Steps

A solution consisting of 3-hydroxy-4-methylpyridine (32.7 g.), 30% aqueous dimethylamine (46.5 ml.) and formalin (25 ml.) in water (50 ml.) was heated on a steam bath for a period of two hours. The cooled reaction solution was then extracted with ten-100 ml. portions of diethyl ether and the combined ether and extracts were subsequently dried over anhydrous magnesium sulfate and filtered. After removal of the volatile liquids by means of evaporation under reduced pressure, there was finally obtained an oil as residue which was subsequently distilled in vacuo to give pure 2-dimethylaminomethyl-3-hydroxy-4-methylpyridine (yield, 34.5 g.), b.p. 71°-74° C./0.6 mm. Hg. The corresponding dihydrochloride salt melted at 214°-217° C. (decomp.) after recrystallization from ethanol/diethyl ether.

Provenance & Evidence