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

HRID 968562

Reaction equation

HRID 968562 reaction equation
Br[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([Br:11])=[CH:4][N:3]=1.[CH3:12][N:13](C)C(=O)C>O>[Br:11][C:5]1[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([C:12]#[N:13])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 31374DimethylacetamideHCID 2984702,5-Dibromo-3-nitropyridine

Product 1

HCID 27696985-Bromo-3-nitropyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Heat a solution of 2,5-dibromo-3-nitropyridine (1.77 g, 6.3 mmol; Malinowski (1988) Bull. Soc. Chim. Belg. 97:51; see also U.S. Pat. No. 5,801,183) and cuprous cyanide (0.60 g, 6.69 mmol) in N,N-dimethylacetamide (25 mL) at 100° C. for 72 hours. After cooling, dilute the mixture with water (25 mL) and extract twice with EtOAc (25 mL each), then wash twice with water (25 mL each). The combined EtOAc extracts are dried (Na2SO4), evaporated, and purified by flash chromatography (50% EtOAc-hexane) to obtain 5-bromo-3-nitropyridine-2-carbonitrile as a pale solid.

Workup

  1. temperatureAfter cooling
  2. extractionextract twice with EtOAc (25 mL each)
  3. washwash twice with water (25 mL each)
  4. dry with materialThe combined EtOAc extracts are dried (Na2SO4)
  5. customevaporated
  6. custompurified by flash chromatography (50% EtOAc-hexane)

Sources & evidence

ORD record
ord-794d4594877541a581123f5d48253418
Source dataset
uspto-grants-2007_12
Patent number
US07304059B2

Linked notes

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