6-Methoxy-2-methylpyridin-3-amine

Synthesis

5467-69-6

52090-56-9

6-Methoxy-2-methyl-3-nitropyridine (2 g, 0.012 mol) was used as starting material, which was dissolved in H2O/MeOH (1:1, 40 mL) mixed solvent. Subsequently, NH4Cl (2.2 g, 3.5 eq.) and iron powder (2.3 g, 3.5 eq.) were added to the solution. The reaction mixture was stirred at 80 °C for 16 hours. After completion of the reaction, the iron powder was removed by filtration and the filtrate was washed with MeOH. The MeOH was removed from the filtrate by evaporation, diluted with H2O, and then the aqueous phase was extracted with EtOAc (3 x 50 mL). The organic phases were combined and dried with anhydrous Na2SO4. The desiccant was removed by filtration and the solvent was evaporated to dryness to give 2-methoxy-5-amino-6-methylpyridine (1.35 g, 81% yield) as a brown oil. Its nuclear magnetic resonance hydrogen spectrum (1H NMR, CDCl3) data were as follows: δ 6.9 (d, 1H), 6.4 (d, 1H), 3.8 (s, 3H), 2.33 (s, 3H).

References