Hydrochloric Acid → 2-Amino-6-chloro-3-iodopyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(6-chloro-3-iodopyridin-2-yl)pivalamide (17.0 g, 50.2 mmol) in dioxane (80 mL) is added 2 N aqueous HCl (50 mL) and the resulting mixture is stirred at 105° C. for 2 h. After cooling to RT, the reaction mixture is slowly poured into a saturated aqueous NaHCO3 solution (200 mL) and the resulting mixture is extracted with ethyl acetate (400 mL×3). The combined organic extracts are washed with brine (300 mL×3), dried over MgSO4, and solvent is evaporated on a rotary evaporator to provide 6-chloro-3-iodopyridine-2-amine as light brown solid (12.8 g, yield 100%). 1H NMR (300 MHz, DMSO-d6), δ 7.85 (d, J=8.1 Hz, 1H), 6.36 (d, J=8.1 Hz, 1H), 6.50 (br s, 2H). LCMS-ESI (m/z): calcd for C5H4ClIN2 253.9; [M+H]+ found 255.3.

Provenance & Evidence