HCID 19966028, Verbindung → HCID 19966031, Verbindung

HRID 1734891Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1734891
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13](=[O:23])[CH2:14][CH2:15][CH:16]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:7][C:6]=1[N+:24]([O-])=O)([CH3:4])([CH3:3])[CH3:2]>[Zn].C(O)(=O)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13](=[O:23])[CH2:14][CH2:15][CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]2)=[CH:7][C:6]=1[NH2:24])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 1

HCID 19966028HCID 19966028, Verbindung

Produkt 1

HCID 19966031HCID 19966031, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittel2×

Versuchsvorschrift

3.08 g (47.1 mmol) of zinc powder and then 0.32 ml of acetic acid were added to 16 ml of a methanolic solution containing 847 mg (2.36 mmol) of 2-t-butyl-5-(5-cycloheptyl-3-oxopentyl)-1-nitrobenzene (prepared as described in Preparation 6), in an ice bath. The mixture was then stirred for 1 hour. At the end of this time, a further 0.32 ml of acetic acid was added, and the mixture was stirred for a further 1 hour. The reaction mixture was then filtered using a Celite filter aid. The insoluble material was washed with ethyl acetate. The filtrate and the washings were combined, condensed to about 10 ml by evaporation under reduced pressure, and diluted with ethyl acetate to distribute the desired compound between the organic solvent and water. In order to remove the insoluble material, the solution was filtered again using a Celite filter aid and the insoluble material was washed again with ethyl acetate. The organic layer was combined with the washings and washed with a saturated aqueous solution of sodium hydrogen carbonate and then with water. The solvent was then removed by distillation under reduced pressure, to obtain 789 mg (a quantitative yield) of the title compound as an oily substance.

Aufarbeitung

  1. stirringthe mixture was stirred for a further 1 hour
  2. filtrationThe reaction mixture was then filtered
  3. filtrationfilter aid
  4. washThe insoluble material was washed with ethyl acetate
  5. customcondensed to about 10 ml
  6. customby evaporation under reduced pressure
  7. additiondiluted with ethyl acetate
  8. customIn order to remove the insoluble material
  9. filtrationthe solution was filtered again
  10. filtrationfilter aid
  11. washthe insoluble material was washed again with ethyl acetate
  12. washwashed with a saturated aqueous solution of sodium hydrogen carbonate
  13. customThe solvent was then removed by distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-29ea4ca3402b4b00bb063b36c2676b82
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05534529

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