Aniline → Phenyl-1-naphthylamine

Participants

Reaction Conditions

Reaction Steps

To a 200 ml, 3-necked round bottom flask equipped with a thermometer and a Dean-Stark apparatus filled with p-cymene and having a condenser are added 7.45 g (80 mmole) of aniline, 4.82 g (39 mmole) of nitrobenzene, 14.6 g (100 mmole) of 1-tetralone and 65 ml of p-cymene solvent. Also introduced were catalyst and various acid promoters as indicated in Table I. The reaction mixtures were heated at reflux (about 185° C.) for 5 hours while removing the evolving water. Thereafter, the mixture was cooled to room temperature, and the catalyst was filtered out using a Celite (trademark) diatomaceous earth filter. The reaction mixture was analyzed by gas-liquid phase chromatography (GLPC) against a PANA standard. The yields mentioned in Table I are based on conversion of tetralone to PANA.

Provenance & Evidence