4-Trimethylsilyloxyaniline → 2-[1-(2,4,6-Trimethylphenylimino)ethyl]-6-[1-(4-trimethylsiloxyphenylimino)ethyl]pyridine

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Reaction Steps

Monoimine (1, 1.4 g, 5 mmol) and 4-trimethylsiloxyaniline (8, 906 mg, 5 mmol) were dissolved in 50 ml of toluene. To this solution 4 Å molecular sieves were added. After standing at room temperature for 4 days with addition of more molecular sieves the reaction mixture was filtered and the solvent was removed in vacuo. The product was washed with a small amount of methanol. Yield 1.4 g (63%) of mixed diimine (9). 1H NMR (CDCl3) δ 8.42 (dd, 1H), 8.33 (dd, 1H), 7.86 (t, 1H), 6.88 (s, 2H), 6.86 (d, 2H), 6.74 (d, 2H), 2.42 (s, 3H), 2.28 (s, 3H), 2.21 (s, 3H), 2.00 (s, 6H), 0.27 (s, 9H).

Provenance & Evidence