4-Methylbenzylamine → 2-benzamido-N-(4-methylbenzyl)-isonicotinamide

Participants

Reaction Steps

Following the procedure as described in Example 1, making variations as required to replace (4-(trifluoromethyl)phenyl)methanamine with p-tolylmethanamine to react with 2-benzamidoisonicotinic acid, 2-benzamido-N-(4-methylbenzyl)-isonicotinamide was obtained as a colorless solid in 35% yield: mp 135-138° C. (dichloromethane/hexanes); 1H NMR (300 MHz, DMSO-d6) δ 11.02 (s, 1H), 9.33-9.30 (m, 1H), 8.60-8.51 (m, 2H), 8.06-8.03 (m, 2H), 7.63-7.50 (m, 4H), 6.25-7.03 (m, 4H), 4.45 (d, J=6.0 Hz, 2H), 2.28 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 166.0, 164.7, 152.8, 148.4, 143.6, 136.1, 135.9, 133.8, 131.9, 128.8, 128.3, 127.9, 127.3, 117.2, 112.7, 42.4, 20.6; MS (ES+) m/z 346.5 (M+1).

Provenance & Evidence