6-Aminonicotinic acid → Methyl 6-aminonicotinate

Participants

Reaction Steps

A solution of 6-aminonicotinic acid (3.0 g, 19 mmol) in HCl/MeOH (2M, 100 mL) was heated at reflux overnight. The solvent was removed under vacuum, and the residue was dissolved in ethyl acetate (200 mL) and washed with aqueous Na2CO3 solution and brine. The organic layer was dried over anhydrous Na2SO4 and concentrated to dryness to give 6-aminonicotinic acid methyl ester as a white solid (2.8 g, 97%), which was directly used in the next step without further purification. 1H NMR (300 MHz, d-DMSO) δ 8.48 (d, J=1.5 Hz, 1 H), 7.79 (dd, J=1.8, 6.6 Hz, 1H), 6.81 (brs, 2H), 6.42 (d, J=6.6 Hz, 1H), 3.73 (s, 3H).

Provenance & Evidence