Pyrrolidine → 4'-Pyrrolidin-1-yl-[2,2';6',2'']terpyridine

Participants

Reaction Steps

28 mg (<5 mol %) of zinc(II) chloride and 4.4 g (61.5 mmol) of pyrrolidine are added in succession to a mixture of 1.1 g (4;1 mmol) of 4′-chloro-[2,2′;6′,2″]terpyridine in 15 ml of 2-methyl-2-butanol. The mixture is heated at reflux for 20 hours, cooled and filtered. After recrystallisation from toluene, pure 4′-pyrrolidin-1-yl-[2,2′;6′,2″]terpyridine is obtained in the form of a white solid. MS (EI, 70 eV): m/z=303 (15); 302 (90, [M+]); 273 (100); 233 (25). 1H-NMR (360 MHz, CDCl3): 1.9–2.0 (m, 4H); 3.39–3.49 (m, 4H); 7.18 (dd, 2H, J=6.7, 5.2 Hz); 7.51 (s, 2H); 7.66–7.76 (tm, 2H); 8.51 (d, 2H, J=7.7 Hz); 8.54–8.60 (m, 2H).

Provenance & Evidence