Sodium Cyanide → Indole-5-carbonitrile

HRID 710293

Reaktionsgleichung

Reaktionsgleichung von HRID 710293
I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[C-:11]#[N:12].[Na+]>CC#N.CCOC(C)=O.[Cu]I>[C:11]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2)#[N:12]

Komponenten

6

Edukt 2

HCID 8929Sodium CyanideHCID 27823135-Iodo-1H-indole

Produkt 1

HCID 27513Indole-5-carbonitrileAusbeute 95,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 5-iodoindole (0.36 g; 1.48 mmol), NaCN (0.15 g; 3 mmol), Pd(Ph3)4 (0.23 g; 0.22 mmol) and CuI (0.06 g; 0.3 mmol) in anhydrous CH3CN (3 ml) was refluxed for 2.5 h under N2. After cooling to room temperature, the mixture was diluted to 20 ml with EtOAc and filtered through a pad of Celite. The filtrate was washed with H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated to dryness under reduced pressure, dissolved in a small volume of CH2Cl2 and filtered through a small pad of SiO2, which was washed with fresh CH2Cl2. The combined filtrates were evaporated to dryness under reduced pressure to give the title compound (0.2 g; 95%) as colourless solid. 1H-NMR (CDCl3) 6.62 (tr, 1H, J=2.5 Hz); 7.33 (tr, 1H, J=2.5 Hz); 7.39-7.47 (m, 2H); 7.98 (s, 1H); 8.51 (broad s, 1H).

Aufarbeitung

  1. temperaturewas refluxed for 2.5 h under N2
  2. filtrationfiltered through a pad of Celite
  3. washThe filtrate was washed with H2O, brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness under reduced pressure
  7. dissolutiondissolved in a small volume of CH2Cl2
  8. filtrationfiltered through a small pad of SiO2, which
  9. washwas washed with fresh CH2Cl2
  10. customThe combined filtrates were evaporated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-06aff8e3d2e940f5acd987d69ad40d19
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181182B2

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