Hydrochloric Acid → 1-(4'-Methoxyphenyl)-1,4-dihydro-indeno[1,2-c] pyrazole

HRID 366385

Reaktionsgleichung

Reaktionsgleichung von HRID 366385
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.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][NH2:23])=[CH:18][CH:17]=1.Cl>C(O)C>[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[C:4]3[C:5]4[C:10]([CH2:11][C:3]=3[CH:2]=[N:23]2)=[CH:9][CH:8]=[CH:7][CH:6]=4)=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 37648821H-Inden-1-one, 2,3-dihydro-2-(hydroxymethylene)-

Produkt 1

HCID 153199401-(4'-Methoxyphenyl)-1,4-dihydro-indeno[1,2-c] pyrazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

2-Hydroxymethylene inden-l-one (Example 1(ii) (a) (4.0 g; 25 mmol), p-methoxyphenyl hydrazine hydrochloride (Aldrich) (4.41 g; 25.25 mmol), 10 M hydrochloric acid (1 cm3) and ethanol (30 cm3), were heated under reflux, for 21 hours. After cooling, the mixture was concentrated in vacuo and the residue dissolved in dichloromethane, then washed with 2M NaOH, dried, filtered and concentrated in vacuo. Purification by column chromatography [Eluant: (dichloromethane: ethanol: ammonia (200:8:1)] Kugelrohr distillation (170° C.; 0.02 mmHg) and recrystallisation (ethanol) afforded needle shaped crystals, m.p. 102-103° C.

Aufarbeitung

  1. temperatureunder reflux, for 21 hours
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated in vacuo
  4. dissolutionthe residue dissolved in dichloromethane
  5. washwashed with 2M NaOH
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by column chromatography [Eluant
  10. distillation(dichloromethane: ethanol: ammonia (200:8:1)] Kugelrohr distillation (170° C.; 0.02 mmHg) and recrystallisation (ethanol)
  11. customafforded needle

Quellen und Nachweise

ORD-Eintrag
ord-2d264ec5b08e4c85957d76acb20b40b8
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06130228

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