“…Synthesis and reactions of alkyl-, aralkyl-, and heteroalkylpyridines The alkylations of 2and 4-picoline, which have been studied by Chichibabin and coworkers (84, page 467; 328), have received much attention in recent years. Thus, 2-picoline (50,88,134,139,196,197,513,571,572,755,822,823,881) and 4-picoline (50,88,139,196,197,210,755,772) have been treated with alkyl halides (50,88,139,196,513,571,572,755,777), olefinic halides (134), dialkylaminoalkyl halides (196,197,823), alicyclic halides (210, 822), 2-thenyl halides (822), haloethers (197), and haloacetals (881) A few of the alkylation studies have given especially interesting results. Brody and Bogert (134) have alkylated 2-picoline with 11-chloro-l-undecene, and, depending on reaction conditions, have obtained one of the isomeric 2-alkylpyridines indicated in the following scheme: Chichibabin (195,196) found that significant amounts of dialkylated products are formed when 2-picolylsodium is treated with alkyl and aralkyl halides.…”