2-Chloro-4-iodo-nicotinic acid methyl ester → Methyl 2-chloro-4-cyanonicotinate

HRID 711457Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 711457
[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8](I)[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:13]([Cu])#[N:14]>CC(N(C)C)=O>[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]([C:13]#[N:14])[C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Komponenten

4

Edukt 2

HCID 108515652-Chloro-4-iodo-nicotinic acid methyl esterHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 58317566Methyl 2-chloro-4-cyanonicotinateAusbeute 34,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

A solution of methyl 2-chloro-4-iodonicotinate (3.20 g, 10.76 mmol) and cyanocopper (0.963 g, 10.76 mmol) in DMA (40 mL) was stirred at 140° C. overnight. Following reaction, the mixture was filtered through Celite and the filtrate was diluted with H2O and EtOAc. The aqueous phase was extracted with EtOAc. The organic phases were combined, washed with H2O and brine, dried over MgSO4, and evaporated. The residue was purified by chromatography on SiO2 (Hexane/EtOAc=10/1) to give the title compound as a white solid (730 mg, 34.5%). 1H NMR (500 MHz, CDCl3) δ ppm 4.07 (s, 3H), 7.57 (d, J=5.37 Hz, 1H), 8.66 (d, J=4.88 Hz, 1H).

Aufarbeitung

  1. customreaction
  2. filtrationthe mixture was filtered through Celite
  3. additionthe filtrate was diluted with H2O and EtOAc
  4. extractionThe aqueous phase was extracted with EtOAc
  5. washwashed with H2O and brine
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customThe residue was purified by chromatography on SiO2 (Hexane/EtOAc=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-8cb5dc0df4a14674886413123041f5b2
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181255B2

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