2-Naphthol → 2-(2-Aminoethoxy)naphthalene

Participants

Reaction Conditions

Reaction Steps

2-naphthol (200 g, 1.39 mol) at room temperature. Potassium hydroxide pellets (8.99 g, 0.139 mol) and 2-oxazolidinone (181 g, 2.08 mol) were then added, and the reaction mixture was heated to reflux and stirred for 5.5 h. Reaction was monitored by TLC analysis. Additional 2-oxazolidinone (24.0 g, 0.277 mol) was added to ensure complete conversion of the 2-naphthol and the reaction mixture was heated to reflux temperature for 16 additional hours. The reaction mixture was cooled to 70° C. and ethylenediamine (18.5 mL, 0.277 mmole) was added. The reaction mixture was then reheated to reflux temperature (approximately 155° C.) under nitrogen and stirred for approximately 6 hours. The reaction mixture was cooled to room temperature and Magnesol® was added and stirred into the reaction mixture for 15 minutes. The reaction mixture was then filtered over Celite® and reaction flask was washed three times with ExxonMobil™ Aromatic 100 solvent. The filtrate was collected and the solvent was evaporated in vacuo to obtain 254.1 g (97%) of 2-(2-naphthoxy)ethylamine. Purity was determined by HPLC and NMR analysis to be ˜92%.

Provenance & Evidence