Nitric Acid → 5-Bromo-2-methyl-4-nitropyridine 1-oxide

Temperature

90 °C

A solution of 5-bromo-2-methyl-pyridine N-oxide (536 mg, 2.85 mmol) in concentrated sulfuric acid (3.0 mL) was added dropwise a solution of fuming nitric acid (2.4 mL) in concentrated sulfuric acid (3.2 mL) at 0° C. The reaction mixture was heated at 90° C. for 1.5 h. The reaction mixture was cooled to rt and poured into ice (50 g). The mixture was extracted with CH2Cl2 (3×20 mL). The combined extracts were washed with a saturated aqueous sodium chloride solution (1×20 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford 5-bromo-2-methyl-4-nitro-pyridine N-oxide as a yellow solid (520 mg, 78%) which was used without further purification

1. temperatureThe reaction mixture was cooled to rt
2. extractionThe mixture was extracted with CH2Cl2 (3×20 mL)
3. washThe combined extracts were washed with a saturated aqueous sodium chloride solution (1×20 mL)
4. dry with materialdried over anhydrous Na2SO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo

ORD record

ord-8f64d7e734f840bc8cceb6a8eb9bef7d

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07803816B2