Hydroxyamine hydrochloride → Methyl 5-(4-bromophenyl)-3-methylisoxazole-4-carboxylate

HRID 553662

Reaktionsgleichung

Reaktionsgleichung von HRID 553662
[CH3:1][O:2][C:3](=[O:17])[CH:4]([C:8](=[O:16])[C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=1)[C:5](=O)[CH3:6].Cl.[NH2:19]O.C([O-])(O)=O.[Na+]>C(O)(=O)C>[CH3:1][O:2][C:3]([C:4]1[C:5]([CH3:6])=[N:19][O:16][C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=1)=[O:17]

Komponenten

5

Edukt 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 603116Methyl acetyl(p-bromobenzoyl)acetate

Produkt 1

HCID 56604575Methyl 5-(4-bromophenyl)-3-methylisoxazole-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

To a mixture of 2-(4-bromo-benzoyl)-3-oxo-butyric acid methyl ester (11 g, 39 mmol) in acetic acid (50 mL) was added hydroxylamine hydrochloride (2.66 g, 39 mmol), and the reaction was stirred at 115° C. for 1 hours. After cooling, saturated aqueous NaHCO3 was added to the mixture to adjust to pH 8. The solution was extracted with EtOAc, and the combined organic layers were washed with brine, dried, filtered, and concentrated to give the title compound.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionThe solution was extracted with EtOAc
  3. washthe combined organic layers were washed with brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-56c451d691a5483883533c782f64ce92
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08048902B2

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