Sulfuric Acid → 2-Acetamido-5-nitropyridine

Temperature

130 °C

To a hot solution of 2-amino-5-nitropyridine (1.4 g, 10 mmol) in acetic anhydride (5 mL) at 100° C. was added conc. H2SO4 (0.1 mL). The resulting mixture was heated at 130° C. for 2 h, cooled and partitioned between EtOAc (200 mL) and water (100 mL). The layers were separated and the aqueous layer was washed once with EtOAc (100 mL). The combined organic layers were washed with water (100 mL), saturated aqueous NaHCO3 (100 mL) and then brine (50 mL); dried over anhydrous MgSO4 and concentrated under reduced pressure to afford N-(5-nitropyridin-2-yl)acetamide (1.8 g, 98%), which was used without further purification. 1H-NMR (CDCl3): δ 9.14 (1H, d), 8.50 (1H, dd), 8.40 (1H, d), 8.23 (1H, br s), 2.29 (3H, s).

1. temperaturecooled
2. custompartitioned between EtOAc (200 mL) and water (100 mL)
3. customThe layers were separated
4. washthe aqueous layer was washed once with EtOAc (100 mL)
5. washThe combined organic layers were washed with water (100 mL), saturated aqueous NaHCO3 (100 mL)
6. dry with materialdried over anhydrous MgSO4
7. concentrationconcentrated under reduced pressure

ORD record

ord-ab83bde488364ac39f79e054ff2ec166

Source dataset

uspto-grants-2004_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06696473B2