Ethylenediamine → 2-(4,5-dihydro-1H-imidazol-2-yl)pyridine

Participants

Reaction Conditions

Reaction Steps

Pyridinecarboxaldehyde (0.95 ml, 10 mmol) is added into a reaction flask containing 20 ml of methylene chloride and ethylene diamine (0.78 ml, 10.5 mmol) is added. After the reaction is carried out at 0° C. for 20 minutes, N-bromosuccinimide (1.87 g, 10.5 mmol) is added. The reaction temperature is slowly raised from 0° C. to the room temperature and the reaction is further carried out for 24 hrs at the room temperature. 10% sodium hydroxide solution is added to have the solution become alkaline. After extraction with a small amount of methylene chloride is carried out for 2 times, the organic layer is collected and concentrated to obtain white solids. After purified by silicone chromatographic column, the product pyil is obtained. The yield is about 90%. 1H NMR (400 MHz, CDCl3): δ 8.55-8.54 (m, 1 H), 8.11 (d, 1 H, J=7.6 Hz), 7.76-7.71 (m, 1 H), 7.34-7.21 (m, 1 H), 3.82 (s, 4 H).

Provenance & Evidence