Acetic Acid → 6-(4-chloro-1H-imidazol-1-yl)-5-methoxypyridin-3-amine

Participants

Reaction Conditions

Reaction Steps

Iron powder-325 mesh (2.19 g, 39.3 mmol) was added to a flask charged with a mixture of 2-(4-chloro-1H-imidazol-1-yl)-3-methoxy-5-nitropyridine (5.0 g, 19.64 mmol), absolute ethanol (50 mL), and glacial acetic acid (20 mL). A water-cooled reflux condenser was attached to the flask and the heterogeneous mixture was heated to 100° C. with vigorous stirring for 30 min. The reaction mixture was allowed to cool to rt and was neutralized upon addition to a chilled and vigorously stirred solution of 5 M NaOH. The resulting mixture was poured into a separatory funnel and extracted with EtOAc. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to afford 6-(4-chloro-1H-imidazol-1-yl)-5-methoxypyridin-3-amine (3.12 g, 71% yield). LC-MS (M+H)+225.1. 1H NMR (500 MHz, CDCl3) δ ppm 8.06 (d, J=1.83 Hz, 1H) 7.53 (dd, J=13.28, 1.98 Hz, 2H) 6.70 (d, J=2.44 Hz, 1H) 3.90 (s, 3H) 3.86 (br. s., 2H).

Provenance & Evidence