Sodium Cyanide → (Quinolin-6-yl)acetonitrile

HRID 401543

Reaktionsgleichung

Reaktionsgleichung von HRID 401543
Br[CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.[C-:13]#[N:14].[Na+]>C(O)C>[N:9]1[C:10]2[C:5](=[CH:4][C:3]([CH2:2][C:13]#[N:14])=[CH:12][CH:11]=2)[CH:6]=[CH:7][CH:8]=1

Komponenten

4

Edukt 2

HCID 8929Sodium CyanideHCID 2243966-(Bromomethyl)quinoline

Produkt 1

HCID 21992552(Quinolin-6-yl)acetonitrileAusbeute 18,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of crude 6-bromomethylquinoline (1.8 g) in 95% ethanol (30 mL) was added NaCN (2.0 g, 40.8 mmol) at room temperature. The mixture was heated at 50° C. for 3 hours and then concentrated under vacuum. Water (50 mL) and ethyl acetate (50 mL) were added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organics were washed with brine, dried over Na2SO4 and concentrated under vacuum. The combined crude product was purified by column (Petroleum Ether/EtOAc 5:1) to give 2-(quinolin-6-yl)acetonitrile (0.25 g, 8% over two steps). 1H NMR (300 MHz, CDCl3) δ 8.95 (dd, J=1.5, 4.2 Hz, 1H), 8.12-8.19 (m, 2H), 7.85 (s, 1H), 7.62 (dd, J=2.1, 8.7 Hz, 1H), 7.46 (q, J=4.2 Hz, 1H), 3.96 (s, 2H). MS (ESI) m/e (M+H)+169.0.

Aufarbeitung

  1. concentrationconcentrated under vacuum
  2. additionWater (50 mL) and ethyl acetate (50 mL) were added
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe combined organics were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under vacuum
  8. customwas purified by column (Petroleum Ether/EtOAc 5:1)

Quellen und Nachweise

ORD-Eintrag
ord-61e3d65ef972495e91d1fbde45d0cfc9
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741933B2

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