Ethyl Acetate → 1-(4-Aminophenyl)cyclopropanecarbonitrile

HRID 1477469Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1477469
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:13]#[N:14])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.CCOC(C)=O>CCO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2([C:13]#[N:14])[CH2:11][CH2:12]2)=[CH:8][CH:9]=1

Komponenten

5

Edukt 2

HCID 8857Ethyl AcetateHCID 43990411-(4-Nitrophenyl)cyclopropanecarbonitrile

Produkt 1

HCID 138269361-(4-Aminophenyl)cyclopropanecarbonitrileAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 1-(4-nitro-phenyl)-cyclopropanecarbonitrile (500 mg, 2.65 mmol, Journal of the American Chemical Society, 71, 2031-5; 1949) in 7 mL of EtOH-2.5 mL of EtOAc was added 350 mg 5% Pd—C. The mixture was stirred under 1 atm of H2 overnight. The reaction was filtered, concentrated in vacuo and then purified using preparative thin layer chromatography (CHCl3) to afford the title compound as an oil (96 mg, 23%). Mass spectrum (ESI, m/z): Cald. C10H10N2, 159.0. found 159.2.

Aufarbeitung

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated in vacuo
  3. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-f78e9843c1a5456c9c98e688cb06866d
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403804B2

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