3-Ethoxy-4-methylisoxazole-5-carboxylic acid → HCID 178431796, compound

HRID 1532019Notes

Reaction equation

HRID 1532019 reaction equation
C([O:3][C:4]1[C:8]([CH3:9])=[C:7]([C:10]([OH:12])=[O:11])[O:6][N:5]=1)C>Br>[OH:3][C:4]1[C:8]([CH3:9])=[C:7]([C:10]([OH:12])=[O:11])[O:6][N:5]=1

Participants

3

Reactant 1

HCID 106787593-Ethoxy-4-methylisoxazole-5-carboxylic acid

Product 1

HCID 178431796HCID 178431796, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

3-Ethoxy-4-methylisoxazole-5-carboxylic acid (15 g, 88 mmol) and 47% HBr (aq) (150 mL) was boiled under reflux for 6 h. The solution was cooled and crystalline title compound was collected by filtration (8.7 g, 69%): mp 257-259° C. The acidic filtrate was added water (100 mL), and extracted with diethyl ether (6×400 mL). The organic extracts were washed with brine (100 mL), dried (MgSO4) and concentrated in vacuo to give crude title compound (3.0 g, 24%). Overall yield of 93%. A mixture of the two crops were used in the next step.

Workup

  1. temperatureunder reflux for 6 h
  2. temperatureThe solution was cooled
  3. filtrationcrystalline title compound was collected by filtration (8.7 g, 69%)
  4. additionThe acidic filtrate was added water (100 mL)
  5. extractionextracted with diethyl ether (6×400 mL)
  6. washThe organic extracts were washed with brine (100 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-16807d7db65f49948185baaab329c411
Source dataset
uspto-grants-2001_03
Patent number
US06200999B1

Reaction notes

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