Pyridine → 2-Amino-4-nitrobenzonitrile

HRID 1041790Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1041790
Br[C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[NH2:4].[N:12]1C=CC=C[CH:13]=1.[Cu]C#N>CN(C=O)C>[NH2:4][C:3]1[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:2]=1[C:13]#[N:12]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 826072-Bromo-5-nitroanilineHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 111478972-Amino-4-nitrobenzonitrileAusbeute 74,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A solution of 2-bromo-5-nitroaniline (10 g, 46 mmol) in DMF (100 mL) and pyridine (40 mL, 490 mmol) was treated with copper(I) cyanide (11.5 g, 128 mmol). The mixture was heated at 160° C. for 2 days under a reflux condenser. After the mixture had cooled to room temperature, it was filtered through celite and washed with ethyl acetate. Concentration and silica gel chromatography using methylene chloride gave 5.57 g of 2-amino-4-nitro-benzonitrile (74%): 1H NMR (300 MHz, CDCl3) δ 7.72 (d, 1H), 7.67 (m, 2H), 4.9 (br, 2H); MS (m/e): 164.1 (M+1).

Aufarbeitung

  1. temperatureAfter the mixture had cooled to room temperature
  2. filtrationit was filtered through celite
  3. washwashed with ethyl acetate
  4. concentrationConcentration and silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7554ddcaf4fb46f7ab6cfeeb24ce05c5
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552186B2

Notizen zur Reaktion

Wird geladen…