Phthalic Anhydride → Ammonium 2-(aminocarbonyl)benzoate

Participants

Reaction Steps

A heterogenous mixture of phthalic anhydride (10.0 g, 67.5 mmol) and 100 mL of dichloromethane was cooled in an ice bath. n-Butyl amine (12.345 g, 168.78 mmol) was added dropwise. The temperature was not allowed to rise above 15° C. during the addition. When a small amount of the amine had been added a homogenous solution resulted. After a short time, a white precipitate formed. As more amine was added, the precipitate redissolved and a solution again formed. Upon completion of the addition the reaction was allowed to stir in an ice bath for 10 minutes. A white precipitate again formed. The mixture was allowed to stir at 0° C. for 50 minutes and at room temperature for 10 minutes. The precipitate was filtered off and washed with a small amount of dichloromethane. Washing with hexanes and drying in air afforded 8.86 g of compound AM-1. NMR was in agreement with the proposed structure.

Provenance & Evidence