Hydrochloric Acid → HCID 11977260, compound

Participants

Reaction Steps

To a mixture of 100 g (0.662 mole) of o-nitrobenzaldehyde and 160 g (1.05 mole) of phosphorus oxychloride was added dropwise with stirring 100 g (1.08 mole) of aniline, keeping the temperature below 30°. After 3 hr. at room temperature it was heated to 75° for 18 hr. and at 90° for 3 hr. (The reaction becomes exothermic when heated). The mixture was cooled, 200ml of ethanol and 200 ml of concentrated hydrochloric acid were added, then heated to reflux for 3 hr. with stirring. On cooling, the precipitate formed was collected and washed with acetone, then resuspended in dilute ammonium hydroxide for 1 hr. and collected again. After crystallization from ethanol, 70 g (86%) of product was obtained. Recrystallization from ethanol gave orange rods, mp 208°-211°.

Provenance & Evidence