5-Aminonicotinic Acid → 5-Hydroxynicotinic acid

Participants

Reaction Steps

A mixture of 4.00 g (29.0 mmol) of 5-aminonicotinic acid in 400 ml of 0.1N H2SO4 at room temperature was diazotized with 2.2 g (31.8 mmol) of NaNO2 by the method of R. Graf (supra) to afford 5-hydroxynicotinic acid. The intermediate free acid was esterified in anhydrous methanolic HCl by the method of Urban (supra) to afford 2.34 g (53% overall yield) of 5-hydroxy nicotinic acid, methyl ester, mp 186°-187° C. (lit 182°-193° C.; Urban, supra). The IR data gave the characteristic 5-hydroxy band at 2550.

Provenance & Evidence