4- n-Amylpyridine

The three picolines react with alkyl halides in liquid ammonia solution in the presence of sodamide to yield the corresponding monoalkylpyridines. a-Picoline also reacts with alkyl chlorides in the presence of sodamide either alone or in the presence of xylene to give a fair yield of monoalkylpyridine CjH N.CHjR. With y-picoliue under similar experimental conditions disubstitution of the alkyl group (CjHjN.CHRj) occurs to an appreciable extent. The preparation of tile three n-amylpyridines is described the 3- and 4-compounds by the liquid ammonia - sodamide method and the 2-compound by the sodamide-3 ene procedure. 

This procedure has been employed by Arens and Wibaut 2 to prepare other 4-alkyl derivatives of pyridine. The yields tend to decrease as the molecular weight of the anhydride increases. The boiling points are as given below 4-propylpyridine 189°, 4-n-butylpyridine 207-209°, 4-isobutylpyridine 197-199°, 4-iso-amylpyridine 222-223°, and 4- -octylpyridine 265-268°. 

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