Abstract
1) Sulfuric acid decomposition of β-phenyl-β-(2-pyridyl)-β-cyanopropionaldehyde diethyl acetal, obtained by the condensation of phenylacetonitrile, 2-bromopyridine, and bromoacetal, yielded β-phenyl-β-(2-pyridyl)-propionaldehyde. p-Chloro derivative was also obtained in a similar manner.
2) The aldoxime obtained by the application of hydroxylamine and β-phenyl-β-(2-pyridyl)-propionaldehyde was reduced and methylated to give 1-phenyl-1-(2-pyridyl)-3-diethylaminopropane.
3) Reductive amination and Leuckart reaction of β-phenyl-β-(2-pyridyl)-propional-dehyde yielded 1-phenyl-1-(2-pyridyl)-3-dimethylaminopropane. 1-(p-Chlorophenyl)-1-(2-pyridyl)-3-aminopropanes, e.g. its N-dimethyl, N-diethyl, N-methyl, and N-ethyl derivatives, were prepared in a similar manner.
4) It was observed that during the formation of p-chlorophenyl-2-pyridylmethane by the sulfuric acid decomposition of p-chlorophenyl-2-pyridylacetonitrile, p-chlorophenyl 2-pyridyl ketone is formed as a by-product.
