Methyl 5-hydroxypyridine-3-carboxylate → Methyl 6-chloro-5-hydroxynicotinate

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Reaction Steps

To a flask containing methyl-5-hydroxynicotinate (4.5 g, 29 mmol) was added sodium hypochlorite aqueous solution (6.15%, 26.7 mL, 22 mmol) dropwise under ice bath cooling. After 30 min of stirring, 2 M HCl (20 mL) was added and the resulting white crystals collected by filtration to give 2.31 g of 6-chloro-5-hydroxynicotinic acid methyl ester in 42% yield. 1H NMR (400 MHz, CDCl3) δ 10.32 (bs, 1H), 8.48 (d, 1H), 7.84 (d, 1H), 7.40 (s, 1H), 3.93 (s, 3H); LC-MS (ELSD): mass calcd for C7H6ClNO3 [M]+ 187. Found 187.

Provenance & Evidence