Water → 5-Bromopyridine-2-carboxylic acid
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#N)=[N:6][CH:7]=1.[OH2:10].[OH-:11].[K+]>CCO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:11])=[O:10])=[N:6][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
5-Bromo-2-pyridinecarbonitrile (1 g, 5.464 mmol) was dissolved in EtOH (20 mL) and water (20 mL) and treated with potassium hydroxide (1.53 g, 27.32 mmol). The reaction mixture was heated to 80° C. for 24 h. The solvent was removed under vacuum and the residue was taken up in water and acidified to pH 4 with 2M HCl. The aqueous layer was extracted with ethyl acetate (×3) and the combined organic layers dried and concentrated to give 5-bromo-2-pyridinecarboxylic acid (0.704 g) as an orange solid which was used in step 2.
Workup
- customThe solvent was removed under vacuum
- extractionThe aqueous layer was extracted with ethyl acetate (×3)
- customthe combined organic layers dried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-362f332401674489971baeed68b4b02b
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853218B2
Reaction notes
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