Ammonium Hydroxide → 2-Amino-4-methylbenzonitrile

HRID 471589

Reaktionsgleichung

Reaktionsgleichung von HRID 471589
Br[C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C([Cu])#[N:12].[NH4+].[OH-]>CN1C(=O)CCC1>[NH2:12][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Komponenten

5

Edukt 3

HCID 14923Ammonium HydroxideHCID 8208022-Bromo-4-methylbenzonitrileHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 28012762-Amino-4-methylbenzonitrileAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 2-bromo-4-methylbenzonitrile (2.0 g, 10.7 mmol) and CuCN (1.92 g, 21.4 mmol) in NMP (10 mL) was reacted in a microwave for 20 min at 200° C. Upon completion the reaction was cooled to 0° C., and 15% aqueous NH4OH (215 mL) was slowly added. The mixture was stirred at rt for 30 min, then extracted with CH2Cl2. The organic layer was washed with H2O, brine, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (3:1 Hexane:EtOAc) to provide 2-amino-4-methylbenzonitrile (1.24 g, 88%). 1H NMR (400 MHz, CDCl3) δ 1.45 (s, 3H), 5.70 (m, 1H), 5.84 (m, 1H), 6.41 (d, J=8.0 Hz, 1H).

Aufarbeitung

  1. extractionextracted with CH2Cl2
  2. washThe organic layer was washed with H2O, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (3:1 Hexane:EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-2e355610288649758aedb4884ecb2884
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633186B2

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