Nitric Acid → HCID 13787609, compound

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.).

1. additionis added dropwise
2. temperaturewith cooling for 0.5 hour
3. temperaturewith cooling
4. filtrationthe precipitate is filtered
5. washwashed with water
6. dissolutiondissolved in 10% sodium bicarbonate (300 ml)
7. extractionThe filtrate is extracted with methylene chloride (3×100 ml)
8. washthe combined methylene chloride extracts are washed with water (3×100 ml)
9. extractionThe methylene chloride layer is extracted with 10% sodium bicarbonate (3×100 ml)
10. washwashed with methylene chloride until the bicarbonate layer
11. temperatureThe bicarbonate solution is cooled in an ice bath
12. filtrationThe precipitated product is filtered
13. washwashed with water
14. customdried in vacuo
15. customRecrystallization from hot hexane yield 4.22 g of product melting at 121°-123° C.(dec.)

ORD record

ord-158c25c859ba448ab894db5c820d9451

Source dataset

uspto-grants-1987_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04643755