Ammonia → 5,8-Dihydronaphthalen-1-amine

Participants

Reaction Steps

1-Aminonaphthalene (79 g, 0.55 mol), ethanol (300 ml), t-butyl alcohol (50 ml), and NH3 (200-300 ml) were placed in a three-necked, round-bottomed flask equipped with a condenser cooled with dry ice. Sodium (30 g, 1.3 mol) was added in portions over a 4 hour period. Then another 50 ml t-butyl alcohol was added. After an hour, 100 ml absolute ethanol was added slowly. This mixture was stirred overnight and then quenched by careful addition of NH4Cl (50 g) and H2O (400 ml). The aqueous and organic layers were separated. The aqueous layer was extracted twice with ether. The ether extracts were combined with the organic layer, which was then extracted with H2O (2x) and sat. NaCl. The organic layer was dried over Na2SO4 and filtered through MgSO4. Following evaporation of ether and most of the t-butyl alcohol at 65° C., colorless 1-amino-5,8-dihydronaphthalene was obtained by vacuum distillation (mp 37°-39° C.; yield 97%).

Provenance & Evidence