Potassium Hydroxide → (E)-3-(imidazo[1,2-a]pyridin-3-yl)acrylic acid
Reaction equation
[OH-].[K+].[N:3]1[CH:4]=[C:5](/[CH:12]=[CH:13]/[C:14]([O:16]CC)=[O:15])[N:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=12>CCO.C1COCC1>[N:3]1[CH:4]=[C:5](/[CH:12]=[CH:13]/[C:14]([OH:16])=[O:15])[N:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=12Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A 1M aqueous solution of KOH (2.2 mL) was added to a solution of (E)-ethyl 3-(imidazo[1,2-a]pyridin-3-yl)acrylate (0.19 g, 0.88 mmol) in EtOH:THF (1:1 v/v) (10 mL). The resulting solution was heated at 50° C. for 3 h. After completion of the reaction the reaction mixture was evaporated and water (10 mL) was added to the residue. This solution was carefully acidified to pH 4 with a 3 M HCl aqueous solution. Since the product, (E)-3-(imidazo[1,2-a]pyridin-3-yl)acrylic acid, was soluble in water, the solution was concentrated under reduced pressure and the solid residue was used directly for the next step. ES+(M+H)+189.
Workup
- customAfter completion of the reaction the reaction mixture
- customwas evaporated
- additionwater (10 mL) was added to the residue
- concentrationthe solution was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-916e9b35f6f642fb85a37597df83b4f7
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08957066B2
Reaction notes
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