Toluene → Methyl 3-aminopyridine-4-carboxylate

Participants

Reaction Steps

3-Aminoisonicotinic acid (400 mg) was suspended in methanol (6 mL) and toluene (18 mL) was added. A solution of (trimethylsilyl)diazomethane (2.0 M in diethyl ether, 1.88 mL) was added slowly to the suspension. Within 5 to 10 minutes after addition, the suspension turned into a solution. After 2 hours stirring at room temperature, the reaction mixture was quenched with water and extracted 3× with ethyl acetate. The combined organic layer was washed with 2N hydrochloric acid, saturated bicarbonate solution and brine, dried over MgSO4 and concentrated in vacuum. The residue was purified by column chromatography (silica gel 60, hexane/ethyl acetate=1:2, Rf=0.40) to afford 340 mg of the title compound of the formula

Provenance & Evidence