Triethylamine → Quinoline

Participants

Reaction Steps

A mixture of 2-aminomethyl-8-hydroxyquinoline hydrochloride (1.05 g, 5 mmol) N-succinimidyl S-tetrahydropyranylmercaptoacetate (1.37 g, 5 mmol), and triethylamine (0.51 g, 5 mmol) in acetonitrile (15 mL) was heated under reflux for 2 hours. The reaction mixture was poured onto water and extracted with methylene chloride (3×20 mL). The combined organic layers were washed with water and dried (MgSO4) to give the ligand of Formula 17 as an orange gum which was sufficiently pure for complexation purposes. 1H-NMR (CDCl3) δ8.42 (broad, 1H), 8.20 (d, 1H), 7.41 (d, 1H), 7.35 (m, 2H), 7.18 (d, 1H), 4.95 (dd, 1H), 4.82(dd, 1H), 4.73 (dd, 1H), 4.00 (m, 1H), 3.78 (m, 1H), 3.57 (d, 1H), 3.35 (d, 1H), 2.10-1.55 (m, 6H); 13C-NMR (CDCl3) δ169.6, 154.1, 152.1, 137.0, 136.9, 127.5, 127.4, 120.2, 117.8, 110.9, 83.7, 65.5, 44.7, 35.2, 30.8, 25.0, 21.6.

Provenance & Evidence