Alkylazines reactions involving essentially complete anion formation

3 Alkylazines reactions involving essentially complete anion formation 

The methyl group of 3-picoline is sufficiently reactive to be alkylated and acylated in this way, although the yields are poor. 

With 2,4-dimethyl-pyridine and -quinoline, selective alkylation or acylation may be achieved at either position. n-Butyllithium promotes ionization at the 2-methyl groups, whereas lithium diisopropylamide reacts at the 4-methyl group. 

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