Pyridine → 3-Iodo-4,5-dimethoxybenzonitrile

HRID 963413Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 963413
[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11])[CH:5]=O.Cl.NO.[N:17]1C=CC=CC=1>C1(C)C=CC=CC=1>[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11])[C:5]#[N:17]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 27781133-Iodo-4,5-dimethoxybenzaldehyde

Produkt 1

HCID 29822483-Iodo-4,5-dimethoxybenzonitrileAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 5.0 g of 3-iodo-4,5-dimethoxy-benzaldehyde, 1.18 g of hydroxylamine hydrochloride, 1.37 g of pyridine and 17 ml of toluene is held at reflux for 2 hrs. (see A. Saednya, Synthesis 1982, 190). The precipitate which separates after cooling is filtered off under suction. Chromatography on silica gel with methylene chloride/methanol 9:1 yields 3.09 g of 3-iodo-4,5-dimethoxy-benzonitrile as a colourless solid. Yield: 63%. Mass spectrum: peaks inter alia at m/e: 289 (100%), 274 (38%), 132 (30%), 119 (43%).

Aufarbeitung

  1. temperatureat reflux for 2 hrs
  2. customSaednya, Synthesis 1982, 190)
  3. temperatureafter cooling
  4. filtrationis filtered off under suction

Quellen und Nachweise

ORD-Eintrag
ord-6b51d522ac9743bc910f2bfe74c018f3
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05763450

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