B. Boduszek, AMINOPHOSPHONIC ACIDS BEARING HETEROCYCLIC MOIETY - PART 4 - SYNTHESIS OF 2-PYRIDYL AND 4-PYRIDYLMETHYL-(AMINO)PHOSPHONIC ACIDS, Phosphorus, sulfur and silicon and the related elements, 122, 1997, pp. 27-32
2-Pyridyl and 4-pyridylmethyl(amino)phosphonic acids are not available
by hydrolysis of corresponding phosphonic esters by means of aq. hydr
ochoric acid. During hydrolysis of these esters a cleavage of C-P bond
occurrs, which leads to a repulsion of phosphorus moiety and formatio
n of the corresponding amine. It was found, that silylation of pyridyl
methyl(amino)phosphonic diethyl esters with bromotrimethylsilane and s
ubsequent solvolysis of the silylated product with methanol led to the
expected 2-pyridyl and 4-pyridylmethyl(amino)phosphonic acids in high
yield.