Reaction Steps
A mixture of 1.50 g (4.26 mmol) of 6-(2-{[(2-methylphenyl)amino]methyl}-1-naphthyl)pyridine-2-carbaldehyde and 0.58 g (4.26 mmol) 2,4,6-trimethylaniline in 15 ml of dry ethanol was refluxed for 3 h. The resulting mixture was evaporated to dryness. The product was isolated from the residue by flash chromatography on silica gel 60 (40-63 um; eluent: hexanes-ethyl acetate=5:1, vol.). Yield 1.80 g (90%) of yellow oil. Anal. calc. for C33H31N3: C, 84.40; H, 6.65; N, 8.95. Found: C, 84.62; H, 6.73; N, 8.88. 1H NMR (CDCl3): 8.37 (m, 1H, 3-H in Py), 8.36 (s, 1H, CH═N), 7.97 (m, 1H, 4-H in Py), 7.93 (d, J=8.3 Hz, 1H, 4-H in naphthyl), 7.90 (m, 1H, 8-H in naphthyl), 7.68 (d, J=8.3 Hz, 1H, 3-H in naphthyl), 7.66 (m, 1H, 5-H in Py), 7.49 (m, 1H, 7-H in naphthyl), 7.39-7.44 (5,6-H in naphthyl), 7.03 (m, 1H, 5-H in Ph), 7.01 (m, 1H, 3-H in ortho-tolyl), 6.89 (s, 2H, 3,5-H in mesityl), 6.62 (m, 1H, 4-H in ortho-tolyl), 6.65 (m, 1H, 6-H in ortho-tolyl), 4.27 (m, 2H, CH2N), 3.97 (br. s, 1H, NH), 2.29 (s, 3H, Me in ortho-tolyl), 2.14 (s, 6H, 2,6-Me in mesityl), 2.08 (s, 3H, 4-Me in mesityl).
