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

Temperature

50 °C

To a suspension of 5-chloro-4-iodo-2-nitroaniline 16-1 (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 residue was re-dissolved in ethyl acetate and washed with sodium bicarbonate solution. The organic phase was concentrated to afford the desired product 16-2 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 residue was re-dissolved in ethyl acetate
6. washwashed with sodium bicarbonate solution
7. concentrationThe organic phase was concentrated

ORD record

ord-ed64789a4c8549dcacbdfdf4456c408b

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08410284B2