Pyridine → 3,5-Dimethyl-4-(4-nitrophenyl)-isoxazole

HRID 450090

Reaktionsgleichung

Reaktionsgleichung von HRID 450090
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:14](=O)[CH3:15])[C:11](=[O:13])[CH3:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.NO.[N:20]1C=CC=CC=1>C(O)C>[CH3:15][C:14]1[C:10]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[C:11]([CH3:12])[O:13][N:20]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 35304123-(4-Nitrophenyl)pentane-2,4-dione

Produkt 1

HCID 153732593,5-Dimethyl-4-(4-nitrophenyl)-isoxazoleAusbeute 91,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 3-(4-nitrophenyl)-pentane-2,4-dione (50 mg, 0.22 mmol), hydroxylamine hydrochloride (15 mg, 0.22 mmol) and pyridine (17 mg, 0.22 mmol) in ethanol (10 ml) was heated to reflux overnight. Evaporation of the solvent gave a residue which was partitioned between water and ethyl acetate. The organic layer was separated, washed with water, then brine and dried. Evaporation to dryness yielded 3,5-dimethyl-4-(4-nitrophenyl)-isoxazole (44 mg, 90%) as solid.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customEvaporation of the solvent
  4. customgave a residue which
  5. customwas partitioned between water and ethyl acetate
  6. customThe organic layer was separated
  7. washwashed with water
  8. dry with materialbrine and dried
  9. customEvaporation to dryness

Quellen und Nachweise

ORD-Eintrag
ord-477b9746117b40318123898ec5ede96c
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486962B2

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