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

HRID 1791207Notes

Reaction equation

HRID 1791207 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-5a51a6fbac0844e1938e16615a729bdb
Source dataset
uspto-grants-2006_07
Patent number
US07074799B2

Reaction notes

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