METHYL 6-FORMYLNICOTINATE

Synthesis Reference(s)

Tetrahedron, 64, p. 688, 2008 DOI: 10.1016/j.tet.2007.11.030

Synthesis

General procedure for the synthesis of methyl 6-formylnicotinate from methyl 6-hydroxymethylnicotinate: a mixture of methyl 6-hydroxymethylnicotinate (7 g, 37 mmol) and manganese dioxide (32.3 g, 372 mmol) in dichloromethane (200 mL) was stirred and reacted for 4 hours at 20°C. After completion of the reaction, the mixture was filtered and the filtrate was concentrated. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate = 5/1) to afford methyl 6-formylnicotinate (6 g, 97% yield). Mass spectral data: MS-ESI (m/z): 166.2 ([M + H]+) (LC-MS method C; retention time: 0.36 min).

References

[1] Patent: WO2014/114185, 2014, A1. Location in patent: Page/Page column 126
[2] Patent: US2014/206681, 2014, A1. Location in patent: Paragraph 0782
[3] Molecules, 2014, vol. 19, # 1, p. 102 - 121
[4] Patent: CN104418811, 2017, B. Location in patent: Paragraph 0234-0236
[5] Tetrahedron Letters, 2006, vol. 47, # 39, p. 7025 - 7029