Iodine → 5-Iodo-6-methylpyridin-2-amine

Participants

Reaction Steps

A mixture of 2-amino-6-picoline (5.40 g), periodic acid (2.28 g), and iodine (5.00 g) is heated in a solution of acetic acid (30 mL), water (6 mL), and sulfuric acid (0.9 mL) at 80° C. for 3 h. The reaction is cooled to room temperature and poured into 100 mL 10% aqueous sodium bisulfite. The aqueous solution is extracted with diethyl ether (3×100 mL). The combined organics are washed with 10% NaOH, then dried over Na2SO4, filtered, and concentrated. Purification by chromatography (eluent EtOAc) affords a yellow liquid. The liquid is further dried on the vacuum pump where it crystallizes to afford 2-amino-5-iodo-6-picoline (4.48 g, 38%). Physical characteristics are as follows: 1H NMR (300 MHz, DMSO-d6) δ 7.60, 6.09, 6.05, 2.38.

Provenance & Evidence