2-Naphthalenecarboxaldehyde → beta-Naphthylideneaniline

Participants

Reaction Conditions

Reaction Steps

A solution of β-naphthaldehyde (0.1 mole), nitrobenzene (0.11 mole) and rhodium hydroxide [Rh(OH)3 ] in 50 ml of pyridine were charged into a stainless steel rocking autoclave of 0.5 l capacity. The autoclave was pressurized to 140 atm with carbon monoxide and heated to 170°C for 3 hours. On completion of the reaction period, the pressure vessel was allowed to cool and the gases vented. Work-up of the reaction mixture gave 75% yield of β-naphthylideneaniline, the product being unequivocally identified by mixed melting point and spectroscopic (ir and nmr) comparison with an authentic sample.

Provenance & Evidence