Chemical Properties
Dark Red Oil
Uses
5-METHOXY-PYRIDIN-2-YLAMINE can react with ketones, aldehydes, acids, polyfunctional esters, and halogenated aromatic hydrocarbons, making it an important raw material for organic synthesis.
Synthesis
General procedure for the synthesis of 2-amino-5-methoxypyridine from 2-bromo-3-methoxy-6-nitropyridine: 2-bromo-3-methoxy-6-nitropyridine (1.20 g, 5.15 mmol), hydrazine hydrate (6 mL), Pd/C (10%, 400 mg), and ethanol (40 mL) were mixed and heated to reflux for 45 minutes. Upon completion of the reaction, the mixture was allowed to cool and filtered through Celite. The filtrate was concentrated, water (20 mL) and saturated ammonia (10 mL) were added and extracted with chloroform (2 x 50 mL). The organic phases were combined, dried over anhydrous sodium sulfate and concentrated to give 2-amino-5-methoxypyridine as a colorless solid with a low melting point. Yield: 615 mg (96%).1H NMR (DMSO-d6, 400MHz) δ 7.64 (dd, 1H), 7.10 (dd, 1H), 6.42 (dd, 1H), 5.43 (br.s, 2H), 3.68 (s, 3H).
References
[1] Patent: WO2007/51981, 2007, A1. Location in patent: Page/Page column 57
[2] Patent: WO2007/51982, 2007, A1. Location in patent: Page/Page column 49
[3] Pharmazie, 2000, vol. 55, # 12, p. 907 - 912
[4] Journal of Medicinal Chemistry, 2009, vol. 52, # 3, p. 637 - 645
[5] Australian Journal of Chemistry, 1981, vol. 34, # 4, p. 927 - 932
