2-Bromo-5-methyl-3-nitropyridine → 5-Methyl-3-nitropicolinonitrile

Temperature

70 °C

A round bottom flask was charged with 2-bromo-5-methyl-3-nitropyridine (60.53 g, 278.9 mmol) and CuCN (27.52 g, 307.3 mmol) The flask was evacuated, and back-filled with nitrogen. DMF (150 mL) was added via cannula. The solution was heated to 70° C. for 1.5 h. After cooling to room temperature, the reaction mixture was poured into EtOAc (500 mL) and water (250 mL). Both phases were filtered through a 1 cm bed of celite. The layers were separated, and the organic phase washed with water (2×100 mL) then with a solution of 1:1 sat. aq. NH4Cl/NH4OH (2×100 mL). The combined aqueous layers were extracted with EtOAc (2×200 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo to afford the title compound (36.10 g, 79% yield).

1. customwas evacuated
2. additionback-filled with nitrogen
3. additionDMF (150 mL) was added via cannula
4. temperatureAfter cooling to room temperature
5. additionthe reaction mixture was poured into EtOAc (500 mL) and water (250 mL)
6. filtrationBoth phases were filtered through a 1 cm bed of celite
7. customThe layers were separated
8. washthe organic phase washed with water (2×100 mL)
9. extractionThe combined aqueous layers were extracted with EtOAc (2×200 mL)
10. dry with materialThe combined organic layers were dried over MgSO4
11. concentrationconcentrated in vacuo

ORD record

ord-2987b153ed7340b280e7b2e7032df0b5

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08519135B2