Hydrochloric Acid → Ethyl 5-Hydroxy-4-isoxazolecarboxylate

HRID 2080115Notes

Reaction equation

HRID 2080115 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5](=[CH:11]OCC)[C:6]([O:8]CC)=[O:7])[CH3:2].Cl.NO.C([N:21](CC)CC)C.Cl>C(O)C.O>[CH2:1]([O:3][C:4]([C:5]1[C:6](=[O:7])[O:8][NH:21][CH:11]=1)=[O:15])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6871Diethyl (ethoxymethylene)malonateHCID 8471TriethylamineHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 239539Ethyl 5-Hydroxy-4-isoxazolecarboxylateYield 66%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-Ethoxymethylene-malonic acid diethyl ester (5.00 g, 23.1 mmol), hydroxylamine hydrochloride (4.01 g, 57.8 mmol) and triethylamine (8.06 mL, 57.8 mmol) were dissolved in ethanol (100 mL), the solution was stirred at room temperature for 17 hours, then, the solution was stirred for 4.5 hours under reflux. The reaction solution was cooled to room temperature, water was added, and 1N hydrochloric acid was added until a salt precipitated. The precipitated salt was collected by filtration, and a hydrochloride salt of the title compound (2.39 g, 15.2 mmol, 66%) was obtained as a white solid.

Workup

  1. stirringthe solution was stirred for 4.5 hours
  2. temperatureunder reflux
  3. temperatureThe reaction solution was cooled to room temperature
  4. customprecipitated
  5. filtrationThe precipitated salt was collected by filtration

Sources & evidence

ORD record
ord-8f6b96a04688418ea6287645e743fecb
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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