Phosphorus oxychloride → 6-bromo-2-chloro-N-methyl-4-nitropyridin-3-amine

Temperature

110 °C

A suspension of 2-bromo-5-(methylamino)-4-nitropyridine 1-oxide (3.35 g, 13.51 mmol) in phosphorous oxychloride (35 mL, 374 mmol) was heated at 110° C. After 1 h, the reaction mixture was cooled to r.t. and evaporated to dryness in vacuo. The residue was partitioned between EtOAc (100 mL) and saturated sodium hydrogen carbonate, the layers were separated and the organic layer was washed with brine and dried over MgSO4. The residue was purified by flash column chromatography (SiO2, 0% EtOAc/Hexanes to 30% EtOAc/hexanes) to give 6-bromo-2-chloro-N-methyl-4-nitropyridin-3-amine 2.59.

1. temperaturethe reaction mixture was cooled to r.t.
2. customevaporated to dryness in vacuo
3. customThe residue was partitioned between EtOAc (100 mL) and saturated sodium hydrogen carbonate
4. customthe layers were separated
5. washthe organic layer was washed with brine
6. dry with materialdried over MgSO4
7. customThe residue was purified by flash column chromatography (SiO2, 0% EtOAc/Hexanes to 30% EtOAc/hexanes)

ORD record

ord-f27ea1e480114069932cd0c688d4a9f6

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09376441B2