Uses
2-Hydroxy-6-methyl-5-nitropyridine is a versatile building block that can be used to create a range of compounds, such as 3-Amino-2-methylpyridine, 6-Chloro-2-methyl-3-nitropyridine, etc.
Synthesis
General procedure for the synthesis of 2-hydroxy-6-methyl-5-nitropyridine from 2-amino-5-nitro-6-methylpyridine: (b) 6-amino-3-nitro-2-methylpyridine (20 g, 0.131 mol) was suspended in a mixture of concentrated hydrochloric acid, H2SO4 (23.7 ml) and water (335 ml). H2SO4 (20 ml) was added slowly under cooling in an ice bath, at which point the amine was not completely dissolved. The suspension was poured into ice (100 g), followed by the addition of NaNO2 (13.53 g, 0.196 mol) solution in water (40 ml) drop by drop. Gas escaped during the reaction. The brown suspension was stirred at 10 °C for 1 h. Subsequently, it was filtered and the precipitate was washed with cold water. The resulting brown product was dried in a freeze dryer to give a final 15.78 g of 6-hydroxy-3-nitro-2-methylpyridine in 78% yield.
References
[1] Patent: WO2005/42464, 2005, A1. Location in patent: Page/Page column 33
[2] Journal of Fluorine Chemistry, 2011, vol. 132, # 8, p. 541 - 547
[3] Patent: CN105906621, 2016, A. Location in patent: Paragraph 0020
[4] Journal of the American Chemical Society, 1952, vol. 74, p. 3828,3830
[5] Yakugaku Zasshi, 1952, vol. 72, p. 434
