Hydrochloric Acid → 2-Phenyl-1,2,2a,3,4,5-hexahydrobenz[cd]indol-5-one

HRID 1637256Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1637256
C([N:9]1[C:17]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:18](=[O:21])[CH2:19][CH2:20][CH:11]([C:12]=23)[CH:10]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=O)C1C=CC=CC=1.Cl.C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[C:22]1([CH:10]2[CH:11]3[CH2:20][CH2:19][C:18](=[O:21])[C:13]4[C:12]3=[C:17]([CH:16]=[CH:15][CH:14]=4)[NH:9]2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 193483011-Benzoyl-2-phenyl-1,2,2a,3,4,5-hexahydrobenz[cd]indol-5-one

Produkt 1

HCID 193482872-Phenyl-1,2,2a,3,4,5-hexahydrobenz[cd]indol-5-oneAusbeute 111,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A portion (4.25 g) of the compound obtained in Example 1 was dissolved in ethanol (40 ml). To the solution was added conc. hydrochloric acid (40 ml) and the resulting mixture was heated to reflux for 2 hours. After allowing to cool, the mixture was diluted with water, adjusted to pH 9 with potassium carbonate and extracted three times with ethyl acetate. The organic layers were combined, washed with saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure and the residue was crystallized from an ether/hexane mixed solvent to yield 3.33 g (92%) of the titled compound as crystals.

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperatureto cool
  4. extractionextracted three times with ethyl acetate
  5. washwashed with saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThen, the solvent was distilled off under reduced pressure
  8. customthe residue was crystallized from an ether/hexane mixed solvent

Quellen und Nachweise

ORD-Eintrag
ord-0fe79847ea854760944a0e9f26b3988d
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06040331

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