2-Methoxypyridin-3-amine

The nitro precursor compound (20.8 g, 135 mmol) was dissolved in methanol (270 mL), and palladium on carbon (10% Pd dry weight, Degussa type E101 NE/W, 50% water content, 5.75 g, 2.7 mmol Pd) was added. The air in the reaction flask was replaced with hydrogen (switching between vacuum and hydrogen from a balloon five times). The mixture was stirred overnight and then filtered. The filtrate was concentrated under vacuum, and the residue was dissolved in a 1:1 mixture of hexane and ethyl acetate and washed with water and saturated sodium bicarbonate. The organic layer was separated, dried over anhydrous magnesium sulfate, and filtered to remove the magnesium sulfate precipitate. The filtrate was concentrated under reduced pressure to give the target product, 2-Methoxypyridin-3-amine (12.43 g, 74%), as a white solid. Figure 2. Synthetic route of 2-Methoxypyridin-3-amine.

2-Methoxy-3-aminopyridine can be used as an intermediate in pharmaceutical chemistry and organic synthesis. In synthetic transformations, the amino group on the pyridine ring can be diazotized and then further derivatized, for example, by in-situ reduction to hydrazine compounds. Furthermore, under appropriate halogenation conditions, a halogen atom can be introduced at the fourth position of pyridine.

Reddish brown solid

ChEBI: 2-Methoxypyridin-3-amine is an aminopyridine.

[1] Tetrahedron, 1997, vol. 53, # 37, p. 12505 - 12524
[2] Patent: US2011/237791, 2011, A1. Location in patent: Page/Page column 63
[3] Patent: US5652363, 1997, A
[4] Patent: WO2005/26137, 2005, A2. Location in patent: Page/Page column 233
[5] Bulletin de la Societe Chimique de France, 1992, # 1, p. 79 - 84