Potassium Iodide → 2-Amino-3-iodo-5-nitropyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-amino-5-nitropyridine (86.3 g, 0.625 mol) and potassium iodate (53.5 g, 0.25 mol) in 2 M sulfuric acid was heated at 100° C. and a solution of potassium iodide (100 g, 0.603 mol) in water (250 mL) was added dropwise over 1 h. The resulting brown mixture was refluxed for 12 h. After being cooled to room temperature, the mixture was adjusted to pH 7 by careful addition of solid sodium bicarbonate. The mixture was extracted with dichloromethane, washed with a saturated sodium thiosulfate solution, dried over anhydrous sodium sulfate, and the solvent removed in vacuo to afford 2-amino-3-iodo-5-nitropyridine (89.3 g, 60%) as a yellow solid: LC/MS m/e calcd for C5H4IN3O2 [M+H]+ 266.01, observed 266.

Provenance & Evidence