2-Nitro-4-toluonitrile → 2-Amino-4-methylbenzonitrile

HRID 442962

Reaktionsgleichung

Reaktionsgleichung von HRID 442962
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([N+:10]([O-])=O)[CH:3]=1>[Pd].O1CCOCC1>[NH2:10][C:4]1[CH:3]=[C:2]([CH3:1])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

Komponenten

4

Edukt 1

HCID 962352-Nitro-4-toluonitrile

Produkt 1

HCID 28012762-Amino-4-methylbenzonitrileAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 4-methyl-2-nitrobenzonitrile (4.9 g, 30 mmol) and 10% palladium on carbon (500 mg) in 1,4-dioxane (60 mL) was stirred under hydrogen (balloon) overnight. The catalyst was removed by filtration through the Celite, and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography (dichloromethane) to give the title compound as a pale yellow solid (3.3 g, 83%). 1H-NMR (300 MHz, CDCl3) δ 7.26 (d, J=8.3 Hz, 1H), 6.56 (s, 1H), 6.55 (s, 1H), 4.32 (br s, 2H), 2.29 (s, 3H).

Aufarbeitung

  1. customThe catalyst was removed by filtration through the Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by flash chromatography (dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-9cfd7fd935834a369adcceeb8e01b05c
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05891909

Verknüpfte Notizen

Wird geladen…