Aniline → 6-bromo-N-phenylnaphthalen-2-amine

Participants

Reaction Conditions

Reaction Steps

Xylene was distilled from a mixture of 6-bromo-2-naphthol (16.4 g., 0.0735 mol.), aniline (25 ml, 0.274 mol.), xylene (25 ml), and p-toluene sulfonic acid monohydrate (2.7 g., 0.014 mol.) until the reaction temperature reached 190° C. The mixture was held at this temperature for 5 hours, and then cooled to 85° C. Sodium acetate (3.7 g.) and ethanol (100 ml) were added and the mixture was heated to reflux. The solution was cooled to 5° C. and the resulting slurry was filtered. The solids were washed with cold ethanol (50 ml). The air-dried solids (19.5 g.) were reslurried in hot water (150 ml) and filtered to give a gray solid, 19.3 g, 88% yield, m.p. 126.2-128.3° C. Two successive recrystalizations from heptane-ethyl acetate (19:1) gave a sample for analysis, m.p. 131-133° C. Mass Spec: m/z 297, 299 (M+). Analysis: Calculated for C16H12NBr: C, 64.45; H, 4.06; N, 4.70, Br, 26.80. Found: C, 64.36; H, 4.02; N, 4.67; Br, 27.04.

Provenance & Evidence