New process for the synthesis of methylamides of 3 - phenyl - 3 - (4 - pyridyl) - 3 - hydroxypropionic and 3 - phenyl - 3 - (2 - pyridyl) - 3 - hydroxypropionic

摘要

The ethyl ester of 3-phenyl-3(4-pyridyl)-3-hydroxy propionic acid and 3-phenyl-3(2-pyridyl)-3-hydroxypropionic acid are made by reacting 4-benzoyl pyridine or 2-benzoyl pyridine with ethyl chloroacetate in the presence of sodium ethoxide, treating the resulting glycidic ester with anhydrous HCl to give the ethyl esters of 2-chloro-3-phenyl-3(4-pyridyl)-3-hydroxy-propionic acid or 2-chloro-3-phenyl-3(2-pyridyl)-3-hydroxypropionic acid, and dehalogenating this compound by hydrogenation in an alcoholic solution in the presence of palladium oxide supported on calcium carbonate. The ethyl esters may be converted to the corresponding N-methyl amides by treatment with 40% by wt. aqueous methylamine.