Methyl iodide → 4-(4-(Dimethylamino)-3-fluorophenyl)-1-methylpyridinium iodide

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Reaction Steps

2-Fluoro-N,N-dimethyl-4-(pyridin-4-yl)aniline (0.5 g, 2.3 mmols) was dissolved in acetonitrile (50 ml) and methyl iodide (3 ml) was added. The mixture was heated at reflux for 2 hrs. This was cooled to ambient temperature and evaporated the product was purified by recrystallization from ethanol/diethyl ether. To give 0.2 g of 4-(4-(dimethylamino)-3-fluorophenyl)-1-methylpyridinium iodide 21% yield as a red solid. 1H NMR (DMSO-d6) δ 3.0 (s, 6H), 4.25 (s, 3H), 7.02 (t, 1H), 7.90 (m, 2H), 8.90 (d, 2H), 8.90 (d, 2H).

Provenance & Evidence