Acetonitrile → 5-Bromo-3-nitropyridine-2-carbonitrile

Heat a solution of 2-amino-5-bromo-3-nitropyridine (2.18 g, 10 mmol), cuprous cyanide (1.33 g, 15 mmol) and tert-butylnitrite (2.0 mL, 15 mmol) in acetonitrile (50 mL) to 60° C. for 2 hours. Cool the solution and partition between ethyl acetate (100 mL) and saturated aqueous NaHCO3 (100 mL). Extract the aqueous solution with ethyl acetate (2×50 mL), wash with water (100 mL), brine (100 mL), dry (MgSO4) and evaporate. Purify the solid by flash chromatography on silica gel (25% ether/75% hexane) to obtain the title compound as a pale yellow solid (934 mg, 41%).

1. temperatureCool the solution
2. custompartition between ethyl acetate (100 mL) and saturated aqueous NaHCO3 (100 mL)
3. extractionExtract the aqueous solution with ethyl acetate (2×50 mL)
4. washwash with water (100 mL), brine (100 mL)
5. dry with materialdry (MgSO4)
6. customevaporate
7. customPurify the solid by flash chromatography on silica gel (25% ether/75% hexane)

ORD record

ord-a6b5fb3780714f14b948c387c47db230

Source dataset

uspto-grants-2006_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07074799B2