Reaction of N-(2-halogenoethyl)-N-methylaniline (I) with magnesium under the Grignard condition was investigated to isolate N-methyl-N-ethylaniline (IV), 1, 4-bis-(methylphenylamino) butane (V), N-methylaniline (VI), and 1, 2-bis (methylphenylamino)-ethane (VII), which must have been formed by way of 2-(methylphenylamino) ethylmagnesium halide (II). However, the addition of propionaldehyde in this reaction gave unexpected 1, 3-dimethyl-2-ethyl-1, 2-dihydroquinoline (IX) instead of the Grignard additon product (VIII). Related reactions are also described.
