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

Participants

Reaction Conditions

Reaction Steps

Methyl nicotinoylacetate (88 g, 0.5 mol) was dissolved in toluene (200 g), isopropyl alcohol (200 g), and formic acid (98-100%, 1.22 g, 0.03 mol) and heated to 60-65° C. Gaseous ammonia (23 g, 1.35 mol) was bubbled through the solution for 15 minutes. The white suspension was stirred at 65° C. until a homogeneous solution formed. The solution was stirred for two hours at 65° C. and then concentrated (ca. 200 g) at 65° C. The residue was cooled to −5° C. with stirring and methyl 3-amino-3-(3-pyridyl)-2-propenoate crystallized as colorless needles. The process of reducing the volume to 50% followed by cooling was repeated three times with the mother liquors. Filtration, washing with toluene, and drying at 30° C. resulted in 77.74 g (88.8%) of methyl 3-amino-3-(3-pyridyl)-2-propenoate as colorless crystals.

Provenance & Evidence