2-Bromo-4-isopropylaniline → 2-Amino-5-isopropylbenzonitrile

HRID 131322

Reaktionsgleichung

Reaktionsgleichung von HRID 131322
[Cu][C:2]#[N:3].Br[C:5]1[CH:10]=[C:9]([CH:11]([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[NH2:14]>CN1CCCC1=O.C(OCC)(=O)C>[NH2:14][C:6]1[CH:7]=[CH:8][C:9]([CH:11]([CH3:13])[CH3:12])=[CH:10][C:5]=1[C:2]#[N:3]

Komponenten

5

Edukt 2

HCID 5213372-Bromo-4-isopropylanilineHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 210934632-Amino-5-isopropylbenzonitrileAusbeute 88,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

Heat a mixture of copper (I) cyanide (2.5 g, 28.02 mmol), and 2-bromo-4-isopropyl-phenylamine (5.0 g, 23.35 mmol) in 1-methyl-2-pyrrolidinone (20 ml) to 195° C. for four hours. Dilute the reaction mixture with 100 ml of ethyl acetate and the dark solution, wash twice with 28% aqueous ammonium hydroxide, twice with saturated aqueous sodium chloride (brine) and twice with water. Collect the organic layer, dry over sodium sulfate and remove the solvent under reduced pressure. Purify the via flash chromatography eluting with a step gradient starting with hexanes and going to 80% hexanes with 20% ethyl acetate to obtain 3.31 g (20.66 mmol, 88% yield) of the title compound as an orange oil: Mass Spectrum (m/e): 161(M+1).

Aufarbeitung

  1. temperatureHeat
  2. washthe dark solution, wash twice with 28% aqueous ammonium hydroxide, twice with saturated aqueous sodium chloride (brine) and twice with water
  3. customCollect the organic layer
  4. dry with materialdry over sodium sulfate
  5. customremove the solvent under reduced pressure
  6. customPurify the via flash chromatography
  7. washeluting with a step gradient

Quellen und Nachweise

ORD-Eintrag
ord-ddbd8bc91ad648baaf64d5f6433256b3
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384934B2

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