Benzaldehyde → 8-(Phenylmethylidene)-5,6,7,8-tetrahydroquinoline

HRID 18246

Reaktionsgleichung

Reaktionsgleichung von HRID 18246
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:9]1[C:18]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=2[CH:12]=[CH:11][CH:10]=1>C(OC(=O)C)(=O)C>[CH:1](=[C:17]1[C:18]2[N:9]=[CH:10][CH:11]=[CH:12][C:13]=2[CH2:14][CH2:15][CH2:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 240BenzaldehydeHCID 663355,6,7,8-Tetrahydroquinoline

Produkt 1

HCID 540746508-(Phenylmethylidene)-5,6,7,8-tetrahydroquinolineAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7918Acetic AnhydrideLösungsmittel

Versuchsvorschrift

Benzaldehyde (3.59 mL, 35.30 mmole) was added to a solution of 5,6,7,8-tetrahydro-quinoline (4.70 g, 35.30 mmole) in acetic anhydride (25 mL), and the solution was heated to reflux under a nitrogen atmosphere. After overnight at reflux, the reaction was concentrated in vacuo. The residue was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated. The residue was purified by flash chromatography on silica gel (33% EtOAc/hexanes) to give the title compound (4.50 g, 58%) as a waxy yellow solid after drying in vacuo: MS (ES) m/e 222 (M+H)+.

Aufarbeitung

  1. temperaturethe solution was heated
  2. temperatureto reflux under a nitrogen atmosphere
  3. temperatureAfter overnight at reflux
  4. concentrationthe reaction was concentrated in vacuo
  5. additionThe residue was diluted with water
  6. extractionextracted with ethyl acetate
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customThe residue was purified by flash chromatography on silica gel (33% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-567f86177836440aaa9b4f74f8fe4c87
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741339B2

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