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

HRID 45591Notes

Reaction equation

HRID 45591 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)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

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 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 hour. After cooling, aqueous workup provided the title compound, which was used directly in the hydrolysis step.

Workup

  1. temperatureAfter cooling

Sources & evidence

ORD record
ord-279da9bd723a40a8a2cec518d7839aad
Source dataset
uspto-grants-2013_09
Patent number
US08541587B2

Reaction notes

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