Hydrochloric Acid → 6-(Methylamino)-2-pyridylethanol

Participants

Reaction Steps

To 6-[(tert-butoxycarbonyl)methylamino]-2-pyridylethanol (17.9 g, 71 mmole) was added a solution of 4N HCl in dioxane (200 mL). The reaction was stirred at room temperature for 1 h (gentle gas evolution was observed) then was concentrated to dryness. The product as the hydrochloride salt solidified under vacuum. The solid was dissolved in NaCl-saturated 1.0 N NaOH solution (75 mL), and the solution was extracted with Et2O (2×200 mL). The combined organic layers were washed with brine, dried (Na2SO4), and concentrated to afford the title compound (9.12 g, 85%) as a waxy solid: 1H NMR (400 MHz, CDCl3) δ 7.37 (t, 1 H). 6.42 (d, J=7.3 Hz, 1 H), 6.27 (d, J=8.3 Hz, 1 H), 4.62 (br s, 1H), 3.96 (t, 2H). 2.90 (d, J=5.2 Hz, 3H), 2.84 (t, 2H); MS (ES) m/e 153 (M+H)+.

Provenance & Evidence