Sulfuric Acid → HCID 13603942, compound

Participants

Reaction Steps

To a solution of 350 g concentrated sulfuric acid and 350 ml of water, cooled to 0°, 40 g of ethyl 4-(4-aminophenyl)pentanoate was added dropwise, maintaining the temperature at 0°-2°. The mixture was treated dropwise with a solution of 13.66 g of sodium nitrite in 25 ml of water at a rate such that the temperature did not exceed 2°. The solution was added dropwise to a refluxing solution of 387 g of copper sulfate in 600 ml of water over a period of about 30 min and the resultant mixture was heated under reflux for an additional 10 min. The mixture was cooled to room temperature, 800 ml of water was added, and extracted thrice with dichloromethane (additional water was needed to dissolve the salts). The organic phase was washed with water, dried over anhydrous sodium sulfate, filtered and evaporated. The residue was distilled at 129° (0.6 mm) to give 21.05 g (53%) of product, mp 32°-34°.

Provenance & Evidence