Uses
1-Methyl-3,5-dinitro-1H-pyridin-2-one can be used as an organic synthesis intermediate involved in the efficient synthesis of nitrocyclic ether[b]pyridine. It is also a nucleophilic reagent. It reacts with primary amines to produce carbamates in an efficient way without using reducing agents. The electronic defects of the pyridine cation allow this nucleophilic attack.
Synthesis
General procedure for the synthesis of 1-methyl-3,5-dinitro-1H-pyridin-2-one from 1-methyl-2-pyridone: To a stirred mixture of 1-methyl-2-pyridone (33.47 g, 0.306 mol) and concentrated sulfuric acid (300 mL) was added concentrated nitric acid (120 mL) in batches at 100 °C. The reaction mixture was heated at this temperature overnight and then poured into ice (1400 mL). The precipitate was collected by filtration and washed with water to afford 1-methyl-3,5-dinitro-1H-pyridin-2-one (yield: 18.66 g, 30%).1H NMR (400 MHz, CDCl3): δ 9.05 (d, 1H), 8.90 (d, 1H), 3.80 (s, 3H).
References
[1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 20, p. 5392 - 5397
[2] Patent: WO2004/69832, 2004, A2. Location in patent: Page 137-138
[3] Patent: US2011/98311, 2011, A1
[4] Patent: US2012/309758, 2012, A1
[5] Patent: US2015/231142, 2015, A1. Location in patent: Paragraph 0698
