Synthesis
8-Bromo-naphthalene-1-carboxylic acid (10.0 g, 39.8 mmol) was dissolved in CHCl3 (60 mL) and concentrated H2SO4 (20 mL) was added. The mixture was stirred at 45C until all compounds were dissolved. NaN3 (15.52 g, 240.0 mmol, 6.0 eq.) was then added in portions, with successive portions added after effervescence due to the above additions ceased. The mixture was stirred at 45 C for 2 h and added to water (100 mL). The mixture was made alkaline using ammonia and extracted with dichloromethane (4 x 30 mL). The stirred extract was dried with Na2SO4 and evaporated to give 8-bromo-1-naphthylamine as a dark crystalline solid.
