Dimethylamine → 1-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one

Participants

Reaction Steps

8 g (0.35 mol) of sodium are placed in 260 ml of toluene and at 100° made into a suspension using a vibromixer. After cooling to 0°, 17 ml (0.42 mol) of methanol are added dropwise, with cooling, and the mixture is then stirred for 45 minutes at 75°. At 25° and with ice-cooling, a solution of 38.5 ml (0.35 mol) of 3-acetylpyridine and 28 ml (0.35 mol) of ethyl formate in 300 ml of toluene are added dropwise in the course of 45 minutes. The yellow suspension is stirred for 16 hours at 25° and then 23.7 g (0.52 mol) of dimethylamine are added. After the addition of 100 ml of toluene, the mixture is stirred for 45 minutes at 25°, and then at 0° a solution of 20 ml of acetic acid in 150 ml of toluene is added dropwise in the course of 30 minutes and the mixture is then boiled at reflux for 1 hour. After cooling to 25°, the mixture is filtered and washed with 500 ml of toluene/hexane (1:1) and the filtrate is concentrated until crystallisation begins. Cooling to 0°, filtration and drying at 80° under HV yield 3-dimethylamino-1-(3-pyridyl)-2-propen-1one; m.p. 81°-82°.

Provenance & Evidence