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

HRID 553662Notes

Reaction equation

HRID 553662 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
115 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-56c451d691a5483883533c782f64ce92
Source dataset
uspto-grants-2011_11
Patent number
US08048902B2

Reaction notes

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