Acetic Acid → Methyl 3-amino-3-(pyridin-3-YL)prop-2-enoate

Participants

Reaction Conditions

Reaction Steps

A suspension of methyl nicotinoylacetate dihydrochloride (50.0 g, 0.23 mol, dried) and sodium acetate (19.0 g, 0.23 mol) in glacial acetic acid (1.4 g, 0.02 mol), toluene (50 g), and methanol (50 g) was heated to 60-65° C. Ammonia (14.0 g, 0.82 mol) was bubbled through the suspension. After four hours, no starting material was present by HPLC. Two-thirds of the solvents were removed by distillation. The solution was stirred at 0° C. for one hour, and the precipitate was collected by filtration and dried to yield 83% of methyl 3-amino-3-(3-pyridyl)-2-propenoate. The crude product was used as is without further purification.

Provenance & Evidence