Picolinic acid → N-(2-Methyl-2-propanyl)-2-pyridinecarboxamide

Participants

Reaction Conditions

Reaction Steps

To a cooled solution of picolinic acid (3.6 g, 29.2 mmole, Aldrich) and triethylamine (8 mL, 57.4 mmole) in 80 mL of methylene chloride at 0° C. was added pivaloyl chloride (3.8 mL, 30.8 mmole). The mixture was stirred for 1 hour at 0° C., t-butylamine (4.0 mL, 38.1 mmole) was added, and stirring was continued for 1 hour at 0° C. and 1 hour at room temperature. Saturated NaHCO3 (30 mL) was added, the layers were separated, and the aqueous layer was extracted with methylene chloride (2×30 mL). The combined organic solutions were dried and concentrated, and the residue was chromatographed in silica gel, eluting with 30 to 60% ethyl acetate in hexane, to provide 5.2 g of the title compound as an oil. MS: 179 (M+H)+ ; 1H NMR (CDCl3) δ: 8.52 (m, (1H), 8.18 (dm, J=7.5 Hz, 1H), 8.0 (s, br, 1H), 7.84 (dt, J=7.5, 1.5 Hz, 1H), 7.40 (ddd, J=7.5, 5.0, 1.5 Hz, 1H), 1.50 (s, 9H).

Provenance & Evidence