1,3-Cyclohexanedione → 1,2,3,9-Tetrahydro-6-(phenylmethoxy)-4H-carbazol-4-one

HRID 4382

Reaktionsgleichung

Reaktionsgleichung von HRID 4382
[C:1]1(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=O)[CH2:2]1.Cl.[C:10]1([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([NH:24]N)=[CH:20][CH:19]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)C.O>[C:10]1([CH2:16][O:17][C:18]2[CH:19]=[C:20]3[C:21](=[CH:22][CH:23]=2)[NH:24][C:3]2[CH2:4][CH2:5][CH2:6][C:1](=[O:8])[C:2]3=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Komponenten

5

Edukt 2

HCID 104341,3-CyclohexanedioneHCID 3016725(4-(Benzyloxy)phenyl)hydrazine monohydrochloride

Produkt 1

HCID 201524471,2,3,9-Tetrahydro-6-(phenylmethoxy)-4H-carbazol-4-oneAusbeute 38,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

1,3-Cyclohexanedione (3.1 g) and the product of Stage (i) (5.6 g) in ethanol (196 ml) and water (39 ml) was stirred at room temperature for 3 h and then heated to reflux for 14 h. The resulting solution was allowed to cool, poured into water (500 ml) and the precipitate filtered and washed with isopropyl acetate and ether to give a solid. Recrystallisation from methanol gave the title compound as a solid (2.5 g) m.p. 235°-237°.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 14 h
  3. temperatureto cool
  4. filtrationthe precipitate filtered
  5. washwashed with isopropyl acetate and ether
  6. customto give a solid
  7. customRecrystallisation from methanol

Quellen und Nachweise

ORD-Eintrag
ord-78fc489b6c4b4be39c7bb6d9b5564ba7
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04725615

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