73896-36-3

Yellow solid

2-Amino-6-methoxy-3-nitropyridine is used as an intermediate in the drug tetrapazole.

1. 7.78 g (0.144 mol) of sodium methanolate was mixed with 50.0 mL of methanol and the mixture was cooled to 15 °C. 2. 25.0 g (0.144 mol) of 2-amino-6-chloro-3-nitropyridine was slowly added to the above solution while maintaining 15°C. 3. the reaction mixture was heated to 25°-30°C and stirred continuously at this temperature for 4-5 hours. 4. The progress of the reaction was monitored by thin layer chromatography (TLC). 5. Upon completion of the reaction, the reaction mixture was slowly poured into water to precipitate the product. 6. The precipitate was collected by filtration and washed with cold water. 7. After drying, 21.0 g of 2-amino-3-nitro-6-methoxypyridine was obtained in 86.5% yield and 99.0% purity by HPLC. 8. 8. The melting point of the product was 167°-169°C. 9. 9. 1H-NMR (CDCl3) data: δ 3.89 ppm (single peak, 3H, OCH3), 6.14-6.16 ppm (twin peaks, 1H), 8.24-8.27 ppm (twin peaks, 1H), 8.16 ppm (single peak, 2H, -NH2).

[1] Patent: US2006/80790, 2006, A1. Location in patent: Page/Page column 3
[2] European Journal of Medicinal Chemistry, 2016, vol. 117, p. 19 - 32
[3] Journal of Medicinal Chemistry, 1997, vol. 40, # 12, p. 1808 - 1819
[4] Patent: WO2014/57415, 2014, A2. Location in patent: Page/Page column 47