Hydrochloric Acid → 2-(5,6-dichloro-1H-indol-3-yl)acetic acid
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][CH:6]=[C:5]2[CH2:12][C:13]([O:15]CC)=[O:14].[Li+].[OH-].Cl>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][CH:6]=[C:5]2[CH2:12][C:13]([OH:15])=[O:14]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of ethyl 2-(5,6-dichloro-1H-indol-3-yl)acetate (120 mg, 0.44 mmol), LiOH (90 mg, 2.20 mmol) in THF (3 mL) and H2O (1 mL) was stirred at RT for 16 h. The solution was poured into water, adjusted pH to 3-4 with 1N HCl and extracted with ethyl acetate. The organic layer was dried over Na2SO4 and concentrated in vacuo to afford the desired product (90 mg, 84.5% yield) as a yellow solid.
Workup
- extractionextracted with ethyl acetate
- dry with materialThe organic layer was dried over Na2SO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-502ec2f94f184ffabb4eb5afae96a2e2
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09227978B2
Reaction notes
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