Sodium Bicarbonate → 1-amino-2,3-dihydro-4,6-dimethyl-7-hydroxy-2-phenyl-1H-indene

HRID 5002

Reaktionsgleichung

Reaktionsgleichung von HRID 5002
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([OH:12])=[C:7]2[C:3]=1[CH2:4][CH:5]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:6]2=[N:13]O.[H][H].C(=O)(O)[O-].[Na+]>C(O)(=O)C.O.[Pt]=O>[NH2:13][CH:6]1[C:7]2[C:3](=[C:2]([CH3:1])[CH:10]=[C:9]([CH3:11])[C:8]=2[OH:12])[CH2:4][CH:5]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

7

Edukt 3

HCID 516892Sodium BicarbonateHCID 1363428322,3-dihydro-4,6-dimethyl-7-hydroxy-2-phenyl-1H-inden-1-one oximeHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 140303341-amino-2,3-dihydro-4,6-dimethyl-7-hydroxy-2-phenyl-1H-indene

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 82844Platinum oxide (PtO)KatalysatorHCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

3.00 Grams of 2,3-dihydro-4,6-dimethyl-7-hydroxy-2-phenyl-1H-inden-1-one oxime was dissolved in 55 ml of glacial acetic acid, and this solution was subjected to catalytic hydrogenation in the presence of 0.3 g of platinum oxide at room temperature under 4 atmospheric hydrogen gas pressure. The hydrogenation was terminated at the point when the stoichiometric amount of hydrogen was absorbed. The catalyst was removed by filtration and the filtrate thus obtained was concentrated. The residue thus obtained was dissolved in water and the pH of this solution was adjusted to about pH 8 by adding an aqueous solution of sodium bicarbonate, then extracted with 200 ml of chloroform. The chloroform extract was washed with water, dried with anhydrous magnesium sulfate, then concentrated under a reduced pressure. Recrystallized from ethanol to obtain 0.24 g of 1-amino-2,3-dihydro-4,6-dimethyl-7-hydroxy-2-phenyl-1H-indene Colorless needlelike crystals. Melting point: 135°-136° C.

Aufarbeitung

  1. customThe hydrogenation was terminated at the point when the stoichiometric amount of hydrogen
  2. customwas absorbed
  3. customThe catalyst was removed by filtration
  4. customthe filtrate thus obtained
  5. concentrationwas concentrated
  6. customThe residue thus obtained
  7. extractionextracted with 200 ml of chloroform
  8. extractionThe chloroform extract
  9. washwas washed with water
  10. dry with materialdried with anhydrous magnesium sulfate
  11. concentrationconcentrated under a reduced pressure
  12. customRecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-484afa8140964d98ab10e3c32c381780
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05242919

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