Syntheses of Organic Phosphates. III. Syntheses and Properties of 2-Amino-3-pyridylmethyl and 2-Chloro-3-pyridylmethyl Phosphates

Two substituted pyridylmethyl phosphates, 2-amino-3-pyridylmethyl (I) and 2-chloro-3-pyridylmethyl phosphates (II), were prepared and their properties were discussed. Acid dissociation constants and NMR data suggested that the neutral species of I exists in the zwitterion form consisting of the protonated amino group and the monoanionic phosphate moiety, while that of II in the dihydrogen phosphate form analogous to the simple alkyl phosphates. In addition, physical properties of 2-amino-3-pyridylmethanol and 2-chloro-3-pyridylmethanol, which are respectively precursors of phosphates I and II, as well as l,2-dihydro-2-oxo-3-hydroxymethylpyridine, were examined by IR and NMR measurements.