Benzaldehyde → 8-(Phenylmethylidene)-5,6,7,8-tetrahydroquinoline

Participants

Reaction Steps

A solution of 5,6,7,8-tetrahydroquinoline (18.2 g, 137 mmol), benzaldehyde (17.7 g, 166. mmol), and acetic anhydride (24.5 mL, 254 mmol) was heated at 165° C. for 16 h. The reaction mixture was cooled to room temperature (rt). Crushed ice was added, and the mixture was slowly basified with NaOH (solid and 2 M NaOH) to pH ˜7. The aqueous layer was extracted with hexane/ethyl acetate (1:1 solution) 3 times. The pooled organic layers were dried over magnesium sulfate. The mixture was filtered, and the solvents were removed under vacuum to give 8-benzylidene-5,6,7,8-tetrahydro-quinoline (2) as a brown solid.

Provenance & Evidence