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

HRID 968562

Reaktionsgleichung

Reaktionsgleichung von HRID 968562
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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-794d4594877541a581123f5d48253418
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07304059B2

Verknüpfte Notizen

Wird geladen…