Heteroaromatic Primary Amines and Formaldehyde: the Formation of N-Hydroxymethyl Derivatives

A product study of the reaction of three heteroaromatic primary amines with paraformaldehyde was made: N-hydroxymethylamines were identified in all cases. Two of them yielded also N,N-dihydroxymethyl derivatives. X-ray diffraction structure determination on one of the N-hydroxymethyl derivatives ruled out the presence of internal hydrogen bonding in the solid state, notwithstanding the almost ideally planar arrangement of the aromatic moiety and the amino function.