Potassium Iodide → 3-Iodo-5-(trifluoromethyl)pyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-trifluoromethyl-pyridin-2-ylamine (32.4 g, 0.2 mol) and potassium iodate (17.12 g, 0.08 mol) in 2M sulfuric acid (400 mL) was heated at 100° C. and a solution of potassium iodide (33.2 g, 0.2 mol) in water (83 mL) was added dropwise over 1 h. The resulting mixture was heated to reflux for 12 h. After being cooled to room temperature, the mixture was adjusted to pH 7 with 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 concentrated in vacuo to afford 3-iodo-5-trifluoromethyl-pyridin-2-ylamine (52.5 g, 91%) as yellow solid: LC/MS m/e calcd for C4H3IN2 [M+H]+ 289.01, observed 288.8.

Provenance & Evidence