Hydrochloric Acid → 3-(2-Chlorophenyl)-1-(4-methylphenyl)-1H-indole-6-carboxylic acid
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([O:19]C)=[O:18])=[CH:14][CH:15]=2)[N:10]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)[CH:9]=1.[OH-].[Na+].O.Cl>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([OH:19])=[O:18])=[CH:14][CH:15]=2)[N:10]([C:21]2[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=2)[CH:9]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of methyl 3-(2-chlorophenyl)-1-(4-methylphenyl)-1H-indole-6-carboxylate (0.11 g, 0.28 mmol) in tetrahydrofuran (2.8 mL) was added sodium hydroxide (2.0 M; 1.40 mL, 2.80 mmol). Water (1.5 mL) was added and the mixture was stirred at 50° C. After 18 h, the mixture was cooled to ambient temperature and 1.0 M hydrochloric acid was added until pH<3. The mixture was extracted with ethyl acetate (3×10 mL). The combined organic layer was washed with saturated aqueous sodium chloride (1×10 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (98 mg): LC-MS [M+1]=362.1.
Workup
- temperaturethe mixture was cooled to ambient temperature
- extractionThe mixture was extracted with ethyl acetate (3×10 mL)
- washThe combined organic layer was washed with saturated aqueous sodium chloride (1×10 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-7497f7d84ef949759705cf0cb38fa57e
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08569512B2
Reaction notes
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