Aniline → 2-Norbornylphenylamine

HRID 378177

Reaktionsgleichung

Reaktionsgleichung von HRID 378177
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:8]12[CH2:14][CH:11]([CH2:12][CH2:13]1)[CH2:10][C:9]2=O.N1C2C=CC=CC=2N=N1.[BH4-].[Na+]>CO.O.C1(C)C(C)=CC=CC=1>[C:8]12([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[NH2:1])[CH2:14][CH:11]([CH2:12][CH2:13]1)[CH2:10][CH2:9]2

Komponenten

8

Edukt 4

HCID 6115AnilineHCID 10345Bicyclo(2.2.1)heptan-2-oneHCID 4311764Sodium borohydrideHCID 178418385HCID 178418385, Verbindung

Produkt 1

HCID 541251582-NorbornylphenylamineAusbeute 106,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

In a 250 mL flask equipped with a Dean-Start separator, the following mixture is brought to reflux: 9.3 g of aniline, 12.1 g 2-norbornanone, 13.2 g benzotriazole and 120 mL xylene. After 16 h, the mixture is reduced to dryness, then it is solubilized in 300 mL methanol, and the product is reduced with 6 g NaBH4 at 50° C. for 1 h. The mixture is then poured into 200 mL water and the organic product is extracted with 3×100 mL toluene. The organic phase is recovered, dried over magnesium sulfate, and then reduced to dryness. In this manner, 20 g of the desired amine are produced.

Aufarbeitung

  1. customIn a 250 mL flask equipped with a Dean-Start separator
  2. temperatureto reflux
  3. extractionthe organic product is extracted with 3×100 mL toluene
  4. customThe organic phase is recovered
  5. dry with materialdried over magnesium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-cae0fbda27d04fde94c95b484282019f
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06030555

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