Hydrochloric Acid → 1,4-Dihydro-1-phenylindeno[1,2-c]pyrazole

HRID 366382

Reaktionsgleichung

Reaktionsgleichung von HRID 366382
O[CH:2]=[C:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]1=O.Cl.[C:14]1([NH:20][NH2:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl>C(O)C>[C:14]1([N:20]2[C:4]3[C:5]4[C:10]([CH2:11][C:3]=3[CH:2]=[N:21]2)=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 60962Phenylhydrazine hydrochlorideHCID 37648821H-Inden-1-one, 2,3-dihydro-2-(hydroxymethylene)-

Produkt 1

HCID 108790091,4-Dihydro-1-phenylindeno[1,2-c]pyrazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

2-Hydroxymethlene indan-1-one (Example 1(ii)(a) (6.0 g, 37.5 mmol), phenylhydrazine hydrochloride (Aldrich) (5.48 g, 37.9 mmol), 10 M hydrochloric acid (1 cm3) and ethanol (30 cm3) were stirred under reflux for 19 hours. After cooling, the solvent was evaporated under reduced pressure and the residue dissolved in dichloromethane, then washed with 2M sodium hydroxide. The organic layer was separated, dried (Na2SO4) filtered and concentrated in vacuo. Purification by Kugelrohr distillation afforded an off-white solid (150° C., 0.01 mmHg) m.p. 119-120° C.

Aufarbeitung

  1. temperatureunder reflux for 19 hours
  2. temperatureAfter cooling
  3. customthe solvent was evaporated under reduced pressure
  4. dissolutionthe residue dissolved in dichloromethane
  5. washwashed with 2M sodium hydroxide
  6. customThe organic layer was separated
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification
  11. distillationby Kugelrohr distillation
  12. customafforded an off-white solid (150° C., 0.01 mmHg) m.p. 119-120° C.

Quellen und Nachweise

ORD-Eintrag
ord-380d35a1d5e1462b8e71bdae12a790df
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06130228

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