Sodium Bicarbonate → HCID 23731082, compound

Participants

Reaction Steps

Over a period of 30 minutes, N,N-dimethylmethyleneammonium iodide (Eschenmoser's salt, 435 mg, 2.35 mmol) is added to a solution of ethyl 2,3-dimethyl-8-hydroxy-imidazo[1,2-a]pyridine-6-carboxylate (500 mg, 2.14 mmol) in 15 ml of dichloromethane. The reaction mixture is stirred for 2.5 hours at ambient temperature and the formation of a colourless precipitate is observed. 20 ml portions of saturated sodium hydrogencarbonate solution and dichloromethane are added to the reaction mixture. The aqueous phase is extracted with dichloromethane (3×20 ml). The combined organic phases are washed with water (20 ml), dried over sodium sulfate, and evaporated to dryness. The title compound (578 mg, 93%) is isolated as a greenish foam containing traces of impurities.—1H NMR (CDCl3, 200 MHz): □=1.41 (t, 3 H), 2.40 (s, 12 H), 4.19 (s, 2 H), 4.37 (q, 2 H), 8.04 (s, 1 H).

Provenance & Evidence