2-Bromo-4-methylaniline → 2-Amino-5-methylbenzonitrile

HRID 131312

Reaktionsgleichung

Reaktionsgleichung von HRID 131312
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH2:9].[C:10]([Cu])#[N:11]>CN1C(=O)CCC1>[NH2:9][C:3]1[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[C:10]#[N:11]

Komponenten

4

Edukt 2

HCID 114222-Bromo-4-methylanilineHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 2427782-Amino-5-methylbenzonitrileAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

Combine 2-bromo-4-methyl-phenylamine (8.00 g, 43.0 mmol), CuCN (4.62 g, 51.6 mmol), and NMP (30.0 ml) and stir at reflux. After 75 minutes, cool to ambient temperature, pour the mixture onto ice chips and stir for 1 hour. Remove the resulting precipitate by vacuum filtration. Dissolve the precipitate in NH4OH and extract with dichloromethane. Combine, wash (brine), dry (sodium sulfate), and reduce the extracts to residue. Purify the residue on silica gel using dichloromethane/hexanes (75:25) to give 3.39 g (60%) of an orange solid: mass spectrum (ion spray): m/z=133.1 (M+1).

Aufarbeitung

  1. temperatureat reflux
  2. additionpour the mixture onto ice chips
  3. customRemove the resulting precipitate
  4. filtrationby vacuum filtration
  5. dissolutionDissolve the precipitate in NH4OH
  6. extractionextract with dichloromethane
  7. washCombine, wash (brine)
  8. dry with materialdry (sodium sulfate)
  9. customPurify the residue on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-04bb8768009749168397a3561c82c357
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384934B2

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