Hydrochloric Acid → HCID 178510261, compound

Participants

Reaction Conditions

Reaction Steps

120 ml of water and 15 ml of 35% hydrochloric acid were added to 5.6 g (0.06 mole) of aniline to obtain a solution. The solution was ice-cooled to 0 to 5° C. Thereto was drop-wise added, with stirring, 24 ml of water in which 4.2 g (0.06 mole) of sodium nitrite had been dissolved, after which stirring was conducted for 1 hour. Then, this aqueous diazonium salt solution was dropwise added to 120 ml of a pyridine solution containing 10.2 g (0.06 mole) of diethyl α-cyanosuccinate, with stirring under ice-cooling. After the dropwise addition, the mixture was stirred for 1 hour under ice-cooling and successively for 1 hour at room temperature, to give rise to a reaction. After the reaction, 240 ml of a 2% aqueous sodium hydroxide solution was added, followed by stirring for 2 hours. Then, the reaction mixture was drop-wise added to 240 ml of 35% hydrochloric acid under ice-cooling. The resulting crystals were collected by filtration, washed with 10 ml of water, and dried in a hot-air drier, to obtain 8.4 g of crude, reddish brown crystals of title compound. The crude crystals were recrystallized from diethyl ether-petroleum ether and dried in a hot-air drier, to obtain 5.7 g (yield: 51.3%) of a title compound as light yellow crystals.

Provenance & Evidence