1,2-Dichloroethane → 2-iodo-N-methylisonicotinamide

Participants

Reaction Steps

A round-bottomed flask was charged with 2-iodoisonicotinic acid (0.70 g, 2.81 mmol), HOBt (474 mg, 3.09 mmol) and EDC (593 mg, 3.09 mmol). DMF (4 mL) was added followed by methylamine (2.0M solution in THF, 8.0 mL, 16.0 mmol) and the resultant suspension was stirred at room temperature overnight. The reaction mixture was quenched with water and extracted with 70 mL diethyl ether (2×). The combined organic layers were washed twice with ˜5 mL water and once with ˜5 mL brine then dried over sodium sulfate, filtered and concentrated. The residue was chromatographed over 24 g silica gel with EtOAc/Hexanes (gradient: 0-60% EtOAc). All fractions containing product were combined and concentrated to give 410 mg (56%) of 2-iodo-N-methyl-isonicotinamide as a white solid.

Provenance & Evidence