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

HRID 131315

Reaktionsgleichung

Reaktionsgleichung von HRID 131315
Br[C:2]1[CH:8]=[C:7]([CH:9]([CH3:11])[CH3:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[Cu][C:13]#[N:14]>CN1C(=O)CCC1.O>[NH2:4][C:3]1[CH:5]=[CH:6][C:7]([CH:9]([CH3:11])[CH3:10])=[CH:8][C:2]=1[C:13]#[N:14]

Komponenten

5

Edukt 2

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

Produkt 1

HCID 210934632-Amino-5-isopropylbenzonitrileAusbeute 57,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

Combine 2-bromo-4-isopropyl aniline (7.5 g, 35 mmol) and copper (I) cyanide (3.76 g, 42 mmol) in NMP (30.0 mL) and heat at 200° C. for 2 hours. Cool to ambient temperature and dilute with water (300 mL). Extract with ethyl acetate to give 4.58 g of the crude product. Silica gel chromatography, eluting with methylene chloride, gives 3.20 g of the title compound as a red oil: mass spectrum (ion spray): m/z=161 (M+1); 1H NMR (300 MHz, DMSO-d6): δ 7.21 (m, 2H), 6.73 (d, 1H), 5.79 (s, 2H), 2.73 (quintet, 1H), 1.12 (d, 6H).

Aufarbeitung

  1. extractionExtract with ethyl acetate
  2. customto give 4.58 g of the crude product
  3. washSilica gel chromatography, eluting with methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-979f34385a684c62a65d70af58c882df
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384934B2

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