Lithium hydroxide, monohydrate → 3-chloro-1H-pyrrole-2-carboxylic acid
Reaction equation
[Cl:1][C:2]1[CH:6]=[CH:5][NH:4][C:3]=1[C:7]([O:9]C)=[O:8].O[Li].O>CO.O>[Cl:1][C:2]1[CH:6]=[CH:5][NH:4][C:3]=1[C:7]([OH:9])=[O:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
Methyl 3-chloro-1H-pyrrole-2-carboxylate (18.86 mmol, 1.0 equiv.) was dissolved in MeOH—H2O (2:1, 120 ml); at 0° C., LiOH.H2O (75.4 mmol, 4 equiv.) was added and the mixture was stirred for 16 h at 25° C. The methanol was concentrated under reduced pressure, and the aqueous residue was diluted with water (60 ml) and extracted with ethyl acetate (2×50 ml). The aqueous phase was adjusted to pH 3-4 with 1 M HCl, and the resulting solid was filtered out. Yield: 90%
Workup
- concentrationThe methanol was concentrated under reduced pressure
- additionthe aqueous residue was diluted with water (60 ml)
- extractionextracted with ethyl acetate (2×50 ml)
- filtrationthe resulting solid was filtered out
Sources & evidence
- ORD record
- ord-6abd48602ed34abcbfbd3df20869cd2b
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08492559B2
Reaction notes
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