Methanol → Methyl 6-aminonicotinate

Participants

Reaction Steps

A mixture of 6-aminonicotinic acid (1.0 equiv., 7.24 mmol, 1.00 g) and sulfuric acid (6.00 equiv., 65.16 mmol, 6.39 g) in methanol was refluxed for 24 h. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure and then made alkaline by the addition of a saturated aqueous NaHCO3 solution. The aqueous layer was extracted with ethyl acetate, the combined organic layers were dried with MgSO4 and concentrated in vacuo to give methyl 6-amino-pyridine-3-carboxylate (15) (0.70 g, yield=64%) as a white crystalline product.

Provenance & Evidence