Hydroxyamine hydrochloride → Methyl 5-(3-bromophenyl)isoxazole-3-carboxylate

HRID 1375654Notes

Reaction equation

HRID 1375654 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4](=O)[CH2:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Br:13])[CH:8]=1.Cl.[NH2:18]O>CO>[CH3:1][O:2][C:3]([C:4]1[CH:5]=[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([Br:13])[CH:8]=2)[O:14][N:18]=1)=[O:16]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 17024761Methyl 4-(3-bromophenyl)-2,4-dioxobutanoate

Product 1

HCID 53393795Methyl 5-(3-bromophenyl)isoxazole-3-carboxylateYield 87.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 2,4-dioxo-4-(3-bromophenyl)-butyric acid methyl ester (10.3 g, 36.1 mmol) in anhydrous MeOH (100 mL) was added hydroxylamine hydrochloride (3.8 g, 54.2 mmol). The mixture was then refluxed for 90 min. The reaction mixture was then cooled to room temperature, and ice/water mixture (200 mL) was added. The mixture was stirred for 20 minutes, filtered through a Buchner funnel and washed with cold water. The light yellow solid was dried in vacuum oven to provide the title compound (8.9 g, 87% yield).

Workup

  1. temperatureThe mixture was then refluxed for 90 min
  2. filtrationfiltered through a Buchner funnel
  3. washwashed with cold water
  4. customThe light yellow solid was dried in vacuum oven

Sources & evidence

ORD record
ord-d459cf83cfac40b18a64af6c1b0c1e6c
Source dataset
uspto-grants-2007_01
Patent number
US07169797B2

Reaction notes

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