Methanol → Methyl 2-oxo-1,2-dihydropyridine-3-carboxylate

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Reaction Steps

To a flask is added 2-hydroxynicotinic acid (10 g, 72 mmol), concentrated H2SO4 (2 mL) and MeOH (400 mL), followed by toluene (80 mL). The reaction mixture is heated to reflux overnight with a Dean-Stark trap. After cooling to RT, the mixture is filtered and the filtrate is concentrated. The residue is dissolved in DCM (200 mL), neutralized with saturated aqueous NaHCO3 to pH 7 and extracted with DCM (200 mL) for three times. The combined organic phases are dried and concentrated to give the desired product (8.2 g, 74% yield). MS (m/z): 153.9 (M+H).

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