Toluene → Acetylpyridine diphenylhydrazone

Participants

Reaction Steps

A mixture of 120 ml toluene, 80 ml hexane, 24.2 acetylpyridine, 24.2 g of diphenylhydrazine hydrochloride, and 30 g of anhydrous sodium acetate was stirred and heated at reflux in a flask equipped with a water separator until no more water was being collected (about 2 hours). The reaction mixture was filtered, and the filtrate was distilled under aspirator vacuum at 60° C. The residue was stirred with 100 ml of methanol with cooling to keep temperature between -10 and -20° C. The resulting solid was collected, washed with 100 ml of cold methanol, and was dried in vacuo to give 43 g of acetylpyridine diphenylhydrazone, mp 84° C. νmax in methanol is 358 nm; absorptivity is 6.7×103.

Provenance & Evidence