Sodium Hydroxide → 5-(4-bromo-2-nitrophenyl)-1-cyclopentyl-1H-pyrazole

HRID 69100

Reaktionsgleichung

Reaktionsgleichung von HRID 69100
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)/[CH:9]=[CH:10]/[N:11](C)C)=[C:4]([N+:15]([O-:17])=[O:16])[CH:3]=1.Cl.[CH:19]1([NH:24]N)[CH2:23][CH2:22][CH2:21][CH2:20]1.O.C(OCC)(=O)C.[OH-].[Na+]>C(O)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:24]([CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[N:11]=[CH:10][CH:9]=2)=[C:4]([N+:15]([O-:17])=[O:16])[CH:3]=1

Komponenten

6

Edukt 4

HCID 14798Sodium HydroxideHCID 212349Cyclopentylhydrazine hydrochlorideHCID 22728543Water ethylacetateHCID 86694307HCID 86694307, Verbindung

Produkt 1

HCID 866943065-(4-bromo-2-nitrophenyl)-1-cyclopentyl-1H-pyrazoleAusbeute 72,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere, to a solution of 1.15 g of (2E)-1-(4-bromo-2-nitrophenyl)-3-(dimethylamino)prop-2-en-1-one in 9.2 mL of acetic acid was added 1.05 g of cyclopentylhydrazine hydrochloride, followed by stirring at room temperature for 60 hours. The reaction mixture was poured into a mixture of water/ethyl acetate, followed by adjusting to pH 10 with a 6 M aqueous sodium hydroxide solution. The aqueous layer was separated, and then the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to obtain 940 mg of 5-(4-bromo-2-nitrophenyl)-1-cyclopentyl-1H-pyrazole.

Aufarbeitung

  1. customThe aqueous layer was separated
  2. washthe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-cf396f515aa44bb389aea08b1452c5fb
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822448B2

Verknüpfte Notizen

Wird geladen…