methyl 6-methoxy-5-nitronicotinate → Methyl 5-amino-6-methoxypyridine-3-carboxylate

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Reaction Steps

A solution of methyl 6-methoxy-5-nitronicotinate (5.4 g) in ethyl acetate (120 mL) is hydrogenated using 5% palladium on carbon (1 g) as catalyst. When hydrogen uptake ceased the mixture is filtered through a pad of diatomaceous earth and the filtrate evaporated. The residue is triturated with n-pentane and methyl t-butyl ether to give methyl 5-amino-6-methoxynicotinoate (4.3 g) as a light-brown solid, m.p.108-9° C. [Elemental analysis: C, 52.99; H, 5.49; N, 15.25%. calculated: C, 52.74; H, 5.53; N, 15.38%.]

Provenance & Evidence