Hydrochloric Acid → 4,5-Dichloropyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4,5-dichloro-2-trimethylacetamido-pyridine (0.500 g, 2.02 mmol) and aqueous HCl (6N; 9.5 ml) was heated was heated at 100° C. for 17 h. The reaction mixture was allowed to cool to room temperature, diluted with ice-water (˜15 ml), and the pH of the mixture was adjusted to ˜7.0 with 10% aqueous NaOH. The white precipitate was collected by filtration, washed with water (2×5 ml), and dried in vacuo over P2O5. The title compound was obtained as a white solid (0.284 g, 86%); 1H-NMR (500 Mz, DMSO-d6) 6.44 (s, 2H, NH2, exchangeable with D2O), 6.64 (s, 1H), and 8.03 (s, 1H) (3-H, 6-H); LC-MS (ESI, m/z) 4.37 min—163, 165, 167 [(M+H)+, Cl2 isotopic pattern].

Provenance & Evidence