Hydrochloric Acid → 2-Chloro-5-iodo-3-nitropyridine

To a solution of 5-iodo-3-nitropyridin-2-amine (1.3 g, 4.9 mmol) in concentrated HCl at 0° C. was added sodium nitrite (6.73 g, 97.13 mmol, 20 eq.) stepwise followed by the addition of copper(I) chloride (0.5 g, 4.9 mmol, 1 eq.) and the mixture was stirred at RT for 12 h. The mixture was then poured in to a mixture of ammonium hydroxide and water (1:1) and extracted with ethylacetate (3×150 ml). The combined organic layer was washed with water, aqueous sodium thiosulfate, brine and dried over sodium sulphate. The solvent was distilled off to afford the product in 43% yield (0.6 g).

1. extractionextracted with ethylacetate (3×150 ml)
2. washThe combined organic layer was washed with water, aqueous sodium thiosulfate, brine
3. dry with materialdried over sodium sulphate
4. distillationThe solvent was distilled off
5. customto afford the product in 43% yield (0.6 g)

ORD record

ord-fd868a0cfcec4c8d8f246e32aeb9792f

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09447091B2