3-Aminopyridine → 3-aminopyridin-1-ium-1-olate hydrochloride

Participants

Reaction Steps

To a mixture of pyridin-3-amine (C-1) (10.0 g, 106.3 mmol, 1.0 eq) in DCM (100 mL) at 0° C., m-chloroperoxybenzoic acid (22.0 g, 128 mmol, 1.2 eq) is added in portions (over 15 min). The resulting mixture is allowed to warm to RT and then stirred at RT for 2 h. The reaction is quenched with water (100 mL). The organic phase is separated and the aqueous layer is extracted with DCM (2×100 mL). The resulting aqueous phase is neutralized with concentrated HCl to adjust the pH to 2-3. To this mixture, 1,4-dioxane (100 mL) is added and the resulting mixture is concentrated in vacuo to afford the product, 3-aminopyridine-1-oxide hydrochloride (D-1).

Provenance & Evidence