Iodine → 2-Amino-5-chloro-3-iodopyridine

Participants

Reaction Steps

Silver sulfate (3.40 g, 10.9 mmol) and 2-amino-5-chloropyridine (1 g, 7.8 mmol) was added to a solution of iodine (2.76 g, 10.9 mmol) in ethanol (50 ml) and the reaction mixture stiffed at rt for 72 h. The mixture was filtered, washed with methanol and the filtrate concentrated in vacuo. The residue was partitioned between saturated Na2S2O3 solution (50 ml) and DCM (2×50 ml). The combined organics were dried (MgSO4), concentrated in vacuo and purified by chromatography on silica gel eluting with DCM to give the title compound as a beige solid. δH (CDCl3): 4.95 (2H, br s), 7.84 (1H, d), 7.98 (1H, d).

Provenance & Evidence