Hydrochloric Acid → 10-Formylanthracene-9-carbonitrile

Participants

Reaction Steps

A 25 mL 2-neck RB flask fitted with thermometer, condenser, N2 inlet, bubbler and stirring bar was charged with 10-chloro-9-anthraldehyde (Aldrich, 5 g, 21 mmol, CuCN (Fisher, 2.14 g, 24 mmol), N-methylpyrrolidinone (Aldrich, 100 mL), dry DMF (Aldrich, 15 mL), and bis(triphenylphosphine) palladium dichloride (Fluka Chemical Corp., 255 Hauser Ave., Hauppauge, NY, 11787, 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 hot PhCH3 (1 L) 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