Hydrochloric Acid → 2,1,3-Benzoxadiazole-5-carboxylic acid
Reaction equation
[N:1]1[O:2][N:3]=[C:4]2[CH:9]=[C:8]([C:10]([O:12]CC)=[O:11])[CH:7]=[CH:6][C:5]=12.[OH-].[Na+].Cl>CO>[N:1]1[O:2][N:3]=[C:4]2[CH:9]=[C:8]([C:10]([OH:12])=[O:11])[CH:7]=[CH:6][C:5]=12Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
To a room temperature, stirred solution of ethyl benzo[c][1,2,5]oxadiazole-5-carboxylate (0.7 g, 3.626 mmol) in MeOH (30 mL) was added 10% NaOH solution (6 mL) and the reaction mixture was then stirred at 40° C. for 3 h. The reaction mixture was then acidified to pH ˜2 with 2 N HCl and the aqueous layer was extracted with DCM (3×150 mL). The combined organic extracts were washed with water (100 mL) and brine (100 mL), dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure to afford benzo[c][1,2,5]oxadiazole-5-carboxylic acid (0.49 g, 82%) as a solid.
Workup
- extractionthe aqueous layer was extracted with DCM (3×150 mL)
- washThe combined organic extracts were washed with water (100 mL) and brine (100 mL)
- dry with materialdried over anhydrous Na2SO4
- filtrationfiltered
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-8270fd21dd084a86bff450c915f7570f
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08071595B2
Reaction notes
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