1,4-Dioxane hydrochloride → Ethyl 2-(6-(methylamino)pyridin-2-yl)acetate

Participants

Reaction Steps

A solution of ethyl-6-[(tert-butoxycarbonyl)methylamino]-2-pyridylacetate (10.72 g, 36.42 mmole) in anhydrous dioxane (91 mL) was cooled to the point of partial crystallization of the solvent, and 4 M HCl/dioxane (91 mL, 364.2 mmole) was added. The solution was warmed to RT and stirred for 17 hr, then was concentrated. The resulting light yellow solid was slurried with CH2Cl2/toluene and reconcentrated to leave the title compound (8.48 g, quantitative) as a light yellow powder: 1H NMR (250 MHz, CD3OD) δ7.84 (dd, J=9.0, 7.2 Hz, 1 H), 6.96 (d, J=9.0 Hz, 1 H), 6.78 (d, J=7.2 Hz, 1 H), 4.22 (q, J=7.1 Hz, 2 H), 3.93 (s, 2 H), 3.05 (s, 3 H), 1.27 (t, J=7.1 Hz, 3 H); MS (ES) m/e 195 (M+H)+.

Provenance & Evidence