3-Ethoxy-4-methylisoxazole-5-carboxylic acid → HCID 178431796, compound
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]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
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
- temperatureunder reflux for 6 h
- temperatureThe solution was cooled
- filtrationcrystalline title compound was collected by filtration (8.7 g, 69%)
- additionThe acidic filtrate was added water (100 mL)
- extractionextracted with diethyl ether (6×400 mL)
- washThe organic extracts were washed with brine (100 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-16807d7db65f49948185baaab329c411
- Source dataset
- uspto-grants-2001_03
- Patent number
- US06200999B1
Reaction notes
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