Sulfuric Acid → 5H-Dibenz(b,e)azepine-6,11-dione

Participants

Reaction Conditions

Reaction Steps

A mixture of concentrated sulfuric acid (25.2 mL) and DCM (dichloromethane) (8.4 mL) was cooled to 0° C., anthraquinone (1) (5 g, 24 mmol) was added, then sodium azide (1.84 g, 28.3 mmol) was added in small portions over a 1 h period at 0-5° C. The reaction mixture stirred overnight at room temperature and then poured into ice water (300 mL). The product was filtered off, washed with water till acid-free and dried to give 5H-dibenzo[b,e]azepine-6,11-dione (2) as a white solid (5.3 g, 100%). Data: (m/z)=224 (M+H)+.

Provenance & Evidence