Pyridine → HCID 606375, compound

Participants

Reaction Steps

In a 500 ml round bottom flask fitted with a stirrer, dropping funnel and calcium chloride drying tube was placed recrystallized dibenz[b,f]azepine (33.5 g, 0.173 moles), 200 ml of anhydrous benzene and pyridine (13.6 g, 0.173 moles). Acetyl chloride (~12.3 ml) was then added dropwise to the mixture. A white precipitate formed with disappearance of orange color. After 3 to 4 hours of stirring, the reaction mixture was extracted with three 100 ml portions of 10% hydrochloric acid or until the extract remained acidic. The organic phase was washed with 5% Na2CO3 in water, dried over anhydrous magnesium sulfate, filtered and concentrated. Crystallization from a hexane-chloroform mixture afforded 49 g of 5-acetyl-5H-dibenz[b,f]azepine, m.p. ~121°.

Provenance & Evidence