Ammonium Chloride → 4-Chloro-5-iodobenzene-1,2-diamine

Temperature

50 °C

To a suspension of 5-chloro-4-iodo-2-nitroaniline (36.5 g, 122 mmol) in EtOH (800 mL) and water (150 mL) was added iron powder (38 g, 673 mmol) and NH4Cl (16 g, 306 mmol). The mixture was heated under nitrogen at 50° C. overnight. Additional iron powder (38 g, 673 mmol) and NH4Cl (16 g, 306 mmol) were added and heating was continued for 45 h. The reaction mixture was cooled, filtered and concentrated. The resulting residue was re-dissolved in ethyl acetate and washed with sodium bicarbonate solution. The organic phase was concentrated to afford the desired product as a gray solid, which was used in the next step without further purification.

1. temperatureheating
2. temperatureThe reaction mixture was cooled
3. filtrationfiltered
4. concentrationconcentrated
5. dissolutionThe resulting residue was re-dissolved in ethyl acetate
6. washwashed with sodium bicarbonate solution
7. concentrationThe organic phase was concentrated

ORD record

ord-ca4ef106e17047ae8e06ce1b93002fad

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08895596B2