Dimethylformamide → 4-(4-Fluorophenyl)pyridine-3-carbaldehyde;hydrochloride

Participants

Reaction Conditions

Reaction Steps

The title compound was prepared following the method described in the literature (C. Jutz, W. Muller and E. Muller, Chem. Ber., 1966 99, 2479) for 3-formyl-4-phenylpyridine. ##STR10## Oxalyl chloride (34 ml; 0.39 moles) was added to a stirred solution of dimethylformamide (33 ml; 0.42 moles) in 1,2-dichloroethane (50 ml). To the resulting mixture was added α-methyl-p-fluorostyrene (13.6 g; 0.1 moles) in dichloroethane (20 ml) and the mixture refluxed for 3 hours. After removal of solvent by distillation under reduced pressure, water (150 ml) was added to give a dark brown solution. An aqueous solution of sodium perchlorate was added to this solution causing the di-iminium perchlorate (2) to precipitate. This was filtered off, washed with water, added to an aqueous solution of ammonium chloride (24 g in 190 ml of water) and heated at 100° C. for 1 hour. After allowing to cool, the reaction mixture was extracted with chloroform and the organic layer separated, washed with water, and ethereal HCl added causing the title compound (3) to precipitate as buff coloured crystals (18g; 76% yield based on styrene (1))

Provenance & Evidence