6-METHOXY-PYRIDINE-2-CARBOXYLICACIDMETHYLESTER

Uses

Methyl 6-methoxy-2-pyridinecarboxylate is a useful research chemical.

Synthesis Reference(s)

Tetrahedron Letters, 15, p. 4339, 1974 DOI: 10.1016/S0040-4039(01)92158-6

Synthesis

General procedure for the synthesis of methyl 6-methoxypyridine-2-carboxylate from 6-hydroxypyridine-2-carboxylic acid and iodomethane: 6-hydroxypyridine-2-carboxylic acid (1 g, 7.19 mmol) and silver carbonate (2.2 g, 7.90 mmol) were placed in a round-bottomed flask, and chloroform (20 mL) was added to dissolve. Subsequently, iodomethane (1 mL, 15.81 mmol) was added slowly and dropwise. The reaction mixture was stirred at 60°C for 26 hours. After completion of the reaction, the mixture was filtered and extracted with chloroform. Next, the extract was vacuum filtered and vacuum distilled to remove the solvent. Finally, the residue was purified by column chromatography (eluent ratio of ethyl acetate: hexane = 1:5) to afford the target product methyl 6-methoxypyridine-2-carboxylate (1.25 g, 100% yield).

References

[1] Patent: WO2014/3483, 2014, A1. Location in patent: Page/Page column 34
[2] Organic and Biomolecular Chemistry, 2006, vol. 4, # 6, p. 1071 - 1084
[3] Organic Letters, 2009, vol. 11, # 23, p. 5562 - 5565
[4] Patent: WO2011/79076, 2011, A1. Location in patent: Page/Page column 93