Ammonia → 7-Ethoxy-5,8-dihydronaphthalen-1-amine

Participants

Reaction Conditions

Reaction Steps

Next, to a mixture of (7-ethoxy-1-naphthyl)amine (1.80 g, 9.61 mmol) and tert-butanol (2.13 g, 28.8 mmol) in tetrahydrofuran (20 mL) was collected liquid ammonia (300 mL) at −78° C. To the mixture was added lithium (0.200 g, 28.8 mmol) over 30 minutes and stirred at −78° C. for 1 hour. Methanol and water was added, and the mixture was stirred at room temperature for 16 hours to allow ammonia to evaporate. To the obtained residue was added ethyl acetate. The organic layer was washed with water, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford (7-ethoxy-5,8-dihydronaphthalen-1-yl)amine (1.37 g, 76% yield).

Provenance & Evidence