Uses
2-Methylisonicotinaldehyde belongs to the pyridine group of compounds and is used in the preparation of benzimidazoles and related analogues as sirtuin modulators and in the synthesis of other organic compounds.
Synthesis
2-Methylisonicotinaldehyde is synthesised using methanol as raw material by chemical reaction. The specific synthesis steps are as follows:
A solution of N,N-dimethyl-2-(2-methyl-4-pyridyl)ethenamine (6.4 g, 39 mmol) in methanol (25 ml) was added dropwise to a mixture of sodium periodate (25.2 g, 117 mmol) and methanol (25 ml) at room temperature..
The mixture was stirred at the same temperature for 1 hr..
The precipitates were filtered off, and the filtrate was concentrated..
The residue was combined with water and extracted with ethyl acetate..
The organic layer was washed with saturated brine and dried over magnesium sulfate..
The solvent was evaporated to give the titled compound (3.7 g, 78 percent).1H-NMR (CDCl3) δ: 2.68 (3H, s), 7.51 (1H, d, J = 4.9 Hz), 7.56 (1H, s), 8.76 (1H, d, J = 4.9 Hz), 10.05 (1H, s).
References
[1] Patent: EP1424336, 2004, A1. Location in patent: Page 247
[2] Patent: WO2010/3048, 2010, A1. Location in patent: Page/Page column 131-132
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 16, p. 6942 - 6990
[4] Patent: WO2009/146358, 2009, A1. Location in patent: Page/Page column 98-99
