Sodium Hydroxide → 1-cyclohexylmethyl-7-chloro-1H-indole-3-carboxylic acid
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[CH:8]=[C:7]2[C:18](C(F)(F)F)=[O:19].[OH-:24].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1)[CH:8]=[C:7]2[C:18]([OH:19])=[O:24]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
The mixture of 7-chloro-1-(cyclohexyl)methyl-3-[(trifluoromethyl)carbonyl]-1H-indole (8.6 g, 25.0 mmol) and 4N NaOH (60 ml) in ethanol (40 ml) was stirred at 85° C. for 18 h. The mixture was concentrated in vacuo and the residue was acidified with 5N HCl, then partitioned between dichloromethane and water. The aqueous layer was extracted with dichloromethane and combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The obtained crystals were washed with n-heptane to afford 7-chloro-1-(cyclohexyl)methyl-1H-indole-3-carboxylic acid (6.4 g, 21.9 mmol).
Workup
- concentrationThe mixture was concentrated in vacuo
- custompartitioned between dichloromethane and water
- extractionThe aqueous layer was extracted with dichloromethane
- washwere washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- washThe obtained crystals were washed with n-heptane
Sources & evidence
- ORD record
- ord-1bfa17dc22db43b7ac6b59fbd2f3e78f
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07763732B2
Reaction notes
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