Nitric Acid → HCID 13787609, 화합물

To an ice-cooled solution of 2-bromo-4-chloro-6-iodoaniline (18.05 mmole, 6.0 g) in 200 ml of glacial acetic acid is added dropwise, 90% nitric acid (173.52 mmole, 8.1 ml). The precipitated salt is observed, while continued stirring with cooling for 0.5 hour. Acetic anhydride (8.1 ml) is added dropwise with cooling. The solution darkens and becomes homogeneous. The cooled solution is poured into 600 ml of ice water, the precipitate is filtered, washed with water, then dissolved in 10% sodium bicarbonate (300 ml). The filtrate is extracted with methylene chloride (3×100 ml), and the combined methylene chloride extracts are washed with water (3×100 ml). The methylene chloride layer is extracted with 10% sodium bicarbonate (3×100 ml), and both of the bicarbonate solutions are combined, then washed with methylene chloride until the bicarbonate layer is colorless. The bicarbonate solution is cooled in an ice bath, then acidified with 15% HCl. The precipitated product is filtered, washed with water, then dried in vacuo. Recrystallization from hot hexane yield 4.22 g of product melting at 121°-123° C.(dec.).