Sodium Hydroxide → 5-Chloro-3-methyl-1H-indole-2-carboxylic acid
Reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([C:16]=1[CH3:17])=[CH:14][C:13]([Cl:18])=[CH:12][CH:11]=2)=[O:7])C>CO>[Cl:18][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:6]([OH:7])=[O:5])=[C:16]2[CH3:17]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
2N NaOH (20 mL) was added to a suspension of 5-chloro-3-methyl-1H-indole-2-carboxylic acid ethyl ester (7.0 g, 29.4 mmol) in methanol (50 mL) and the resulting mixture stirred at 25° C. for 18 hours. Tetrahydroturan (100 mL) was added and the resulting solution heated at reflux for 30 minutes and concentrated. The residue was dissolved in water and the resulting solution extracted twice with ethyl acetate. The aqueous layer was acidified and the precipitate collected by filtration and washed with water (5.24 g).
Workup
- additionTetrahydroturan (100 mL) was added
- temperaturethe resulting solution heated
- temperatureat reflux for 30 minutes
- concentrationconcentrated
- dissolutionThe residue was dissolved in water
- extractionthe resulting solution extracted twice with ethyl acetate
- filtrationthe precipitate collected by filtration
- washwashed with water (5.24 g)
Sources & evidence
- ORD record
- ord-a1c5154bd943406f9ca0f7d2bf8fe960
- Source dataset
- uspto-grants-2005_01
- Patent number
- US06846820B2
Reaction notes
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