Formic Acid → 5-[4-chloro-2-(trifluoromethyl)phenyl]-4-methyl-1H-pyrrole-3-carboxylic acid
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][CH:11]=[C:10]([C:13]([O:15]C)=[O:14])[C:9]=2[CH3:17])=[C:4]([C:18]([F:21])([F:20])[F:19])[CH:3]=1.[OH-].[Na+].C(O)=O>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][CH:11]=[C:10]([C:13]([OH:15])=[O:14])[C:9]=2[CH3:17])=[C:4]([C:18]([F:21])([F:19])[F:20])[CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of methyl 5-[4-chloro-2-(trifluoromethyl)phenyl]-4-methyl-1H-pyrrole-3-carboxylate (0.39 g, 1.3 mmol) in methanol (5.0 ml) was added 5N NaOH (5.0 ml) and the mixture was stirred at 80° C. for 3.0 h. The reaction mixture was cooled to room temperature and added formic acid (3.0 ml). The mixture was concentrated on a rotary evaporator. To the residue was added water and triturated. The solid was filtered and dried to give the title compound (0.37 g, 93%) as a brown solid.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- concentrationThe mixture was concentrated on a rotary evaporator
- additionTo the residue was added water
- customtriturated
- filtrationThe solid was filtered
- customdried
Sources & evidence
- ORD record
- ord-c7a725ed2398435f9026879de2baa829
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08487117B2
Reaction notes
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