Ethanolamine → Ammonium Hydroxide

Participants

Reaction Steps

Add sodium hydride (60% in mineral oil, 6.63 g, 166 mmol) to a solution of 2-hydroxyethylamine (10.0 mL, 166 mmol) in dioxane (150 mL), at room temperature under nitrogen. Stir for 10 minutes at room temperature. Add 2-chloropyridine (15.6 mL, 166 mmol) and heat the reaction mixture to reflux. After stirring at reflux for 14 hours, cool the reaction mixture to room temperature and dilute with water (100 mL), and methylene chloride (200 mL). Extract the aqueous layer with methylene chloride (2×100 mL). Combine the organic layers with brine (200 mL), dry (magnesium sulfate), filter and concentrate to an orange oil. Perform flash chromatography on silica gel eluting with 50% of a 80:18:2 CHCl3/MeOH/concentrated NH4OH) solution in methylene chloride to afford the title compound as a yellow oil (17.9 g). MS: m/z=139 (MH+).

Provenance & Evidence