N-Iodosuccinimide → HCID 86710119, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 6-amino-2-methylisonicotinate (2.00 g, 11.1 mmol) was dissolved in DMF (20 mL), and the solution was stirred overnight at 60° C. after adding N-iodosuccinimide (2.50 g, 11.1 mmol). The reaction mixture was stirred at 60° C. for 5 hours after adding N-iodosuccinimide (1.25 g, 5.55 mmol). The reaction mixture was allowed to cool to room temperature, and extracted with a mixed solvent of ethyl acetate and hexane after adding a sodium hydrogen carbonate aqueous solution. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→50/50) to give ethyl 6-amino-3-iodo-2-methylisonicotinate (1.92 g, yield 57%).

Provenance & Evidence