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

Article abstract of DOI:10.1016/0040-4020(95)00442-B

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.