Sodium Iodide → Methyl 4,5,6-trichloro-3-iodopicolinate

Participants

Reaction Conditions

Reaction Steps

Methyl 3-amino-4,5,6-trichloropicolinate (0.5 g, 2.0 mmol) was dissolved in concentrated HCl (20 mL), cooled to 5° C., and treated with a solution of sodium nitrite (0.2 g, 3.0 mmol dissolved in 1 mL of water) over 15 minutes. The reaction mixture was stirred for 20 minutes at 5° C. and poured carefully into a rapidly stirred mixture of sodium iodide (1.8 g; 12 mmol) in water (100 mL) and dichloromethane (30 mL). After 20 minutes, solid sodium bisulfite was added. Ethyl acetate (100 mL) was added and the phases were separated. The organic phase was washed with saturated sodium chloride, dried over sodium sulfate, and concentrated under vacuum. The above procedure was performed again on 1.5 g of the amine and the combined crude products were purified by flash chromatography (SiO2, hexane/ethyl acetate) to afford the title compound as a white solid (1.8 g 61%): mp 61-62° C.; 1H NMR (400 MHz, CDCl3) δ 4.00 (s, 3H); EIMS m/z 365.

Provenance & Evidence