Hydrochloric Acid → 4,5-Dichloro-1H-pyrrole-2-carboxylic acid
Reaction equation
[OH-].[Li+].O.[Cl:4][C:5]1[CH:6]=[C:7]([C:11]([O:13]CC)=[O:12])[NH:8][C:9]=1[Cl:10].Cl>C1COCC1>[Cl:4][C:5]1[CH:6]=[C:7]([C:11]([OH:13])=[O:12])[NH:8][C:9]=1[Cl:10]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A solution of lithium hydroxide in water (2 N, 0.80 ml, 0.16 mol) was added to a stirred solution of a mixture of ethyl 4,5-dichloro-1H-pyrrole-2-carboxylate (Intermediate 59; 7.0 g, 0.033 mol) in THF (15 ml) at room temperature. The mixture was stirred at 50° C. for 8 h over 2 days. The reaction mixture was acidified with 10% HCl solution to a pH ˜2 and partitioned between EtOAc and water. The organic layer was dried over MgSO4 and concentrated in vacuo to give the title compound (4.0 g).
Workup
- custompartitioned between EtOAc and water
- dry with materialThe organic layer was dried over MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-2ca8f833f99c4a22a45efa2d2120dc92
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07709503B2
Reaction notes
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