Acetic Acid → 5,6-Diaminonicotinic acid

Participants

Reaction Conditions

Reaction Steps

See Markwald, W. Chem. Ber. 1984, 27, 1317. To a stirred solution of SnCl2 (4.16 g, 22.0 mmol) in concentrated HCl (11 mL) at 0° C. was added in portions 5-nitro-6-aminonicotinic acid (1.01 g, 5.5 mmol). The resulting orange mixture was then heated to 100° C. under argon for 75 min. The mixture was then cooled to RT and was then placed in an ice bath and neutralized with concentrated aqueous ammonia (to pH 6-7), resulting in a thick cream-colored mixture. The mixture was then acidified to pH 4 with acetic acid and the precipitate collected by filtration, washed with H2O and dried under vacuum overnight to afford the title compound: 1H NMR (300 MHz, DMSO-d6): δ7.98 (d, J=2.1 Hz, 1H), 7.21 (d, J=2.1 Hz, 1H), 6.24 (br s, 2H), 5.00 (br s, 2H).

Provenance & Evidence