Hydrochloric Acid → 10-Formylanthracene-9-carbonitrile

Participants

Reaction Steps

A 250 mL 2-neck round bottom flask fitted with thermometer, condenser, N2 inlet and bubbler, and stirring bar was charged with 10-chloro-9-anthraldehyde (Aldrich, 5 g, 21 mmol, CuCN (Fisher Scientific Company, 711 Forbes Ave., Pittsburgh, PA, 15219, 2.14 g, 24 mmol), N-methylpyrrolidinone (100 mL), DMF (15 mL), and bis(triphenylphosphine)palladium dichloride (Fluka, 0.08 g, 0.1 mmol). The mixture was warmed to 170° and stirred 15 h under N2. After 1.5 h, the mixture became homogeneous. The reaction was cooled to 70° and poured into a solution composed of 16 g of FeCl3.6H2O, (Mallinckrodt), 70 mL of 1.0M HCl and 400 mL H2O. The resulting mixture was stirred at 60°-70° for 1 h, filtered and a crude orange solid isolated. This material was dissolved in 1 L of hot PhCH3 and passed through a small plug (100 g) of SiO2. The filtrate was then concentrated to 75 mL and diluted with hexane (200 mL). The orange solid which formed was collected by filtration and dried at 50° to give 3.17 g (68%) of 10-formyl-9-anthracenecarbonitrile mp 270°-275°, (C, H, N).

Provenance & Evidence