1-Naphthylamine → HCID 22171932, compound

Participants

Reaction Steps

2,6-Diacetylpyridine (5.49 g, 33.6 mmol) and 1-aminonaphthalene (4.8 g, 33.5 mmol) were dissolved in 100 ml of toluene. To this solution molecular sieves (4 Å) were added. After standing for 20 hours at room temperature, the mixture was filtered. The solvent was removed in vacuo. The resulting mixture of 2,6-diacetylpyridine, 2,6-bis-[1-(1-naphthylimino)ethyl] pyridine and 2-[1-(1-naphthylimino)ethyl]-6-acetylpyridine was dissolved in 50 ml THF. The diiminepyridine by-product 2,6-bis-[1-(1-naphthylimino)ethyl]pyridine was removed by selective complexation to a metal halide. FeCl2 (0.79 g , 6.23 mmol) was added in an inert atmosphere. After stirring for 16 hours at room temperature, the solvent was removed in vacuo. Toluene (100 ml) was added to the resulting mixture. The precipitated complex was filtered off over a small layer of silica, yielding a yellow solution. The solvent was removed vacuo. Crystallisation from ethanol yielded 3.25 g of 2-[1-(1-naphthylimino)ethyl]-6-acetylpyridine (6) (33.6%). 1H-NMR (CDCl3) δ 8.65 (d, 1H, Py-Hm), 8.15 (d, 1H, Py-Hm), 7.95 (t, 1H, Py-Hp), 7.87 (d, 1H, ArH), 7.76 (d, 1H, ArH), 7.64 (d, 1H, ArH), 7.4-7.6 (m, 3H, ArH), 6.82 (d, 1H, ArH), 2.79 (s, 3H, Me), 2.38 (s, 3H, Me).

Provenance & Evidence