Pyridine → 1,2,3,4-Tetrahydrocarbazole

HRID 597541

Reaktionsgleichung

Reaktionsgleichung von HRID 597541
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[C:9]1([NH:15]N)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.N1C=CC=CC=1>O>[CH2:5]1[C:6]2[NH:15][C:9]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:1]=2[CH2:2][CH2:3][CH2:4]1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 7967CyclohexanoneHCID 60962Phenylhydrazine hydrochloride

Produkt 1

HCID 136641,2,3,4-Tetrahydrocarbazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

Cyclohexanone (2.0 ml., 0.020 mole), phenylhydrazine hydrochloride (2.88 g., (0.020 mole) and 6.0 ml. of freshly distilled pyridine are combined, heated at reflux (115° C) for 3 hours, then allowed to cool to room temperature and allowed to stir overnight. About 25 ml. of water is added and the precipitated solids are collected by decantation. After washing again with water, the solids are dissolved in a mixture of 20 ml. of ethanol and 5 ml. of water and set aside. The resulting crystals are collected by filtration, washed with aqueous ethanol and dried to afford 2.65 g. (77.5% of theory) of the title compound, M.P. 119°-120° C. A mixture of the product and an authentic sample of 1,2,3,4-tetrahydrocarbazole also melted at 119°-120° C.

Aufarbeitung

  1. temperatureheated
  2. temperatureto cool to room temperature
  3. customthe precipitated solids are collected by decantation
  4. washAfter washing again with water
  5. dissolutionthe solids are dissolved in a mixture of 20 ml
  6. filtrationThe resulting crystals are collected by filtration
  7. washwashed with aqueous ethanol
  8. customdried
  9. customto afford 2.65 g

Quellen und Nachweise

ORD-Eintrag
ord-d32beca789d94ffc8406731eb2d2faf5
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04014890

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