Hydrochloric Acid → 5-[5-(3,4-dichlorobenzoylamino)pyridin-2-yloxy]-1H-indole-2-carboxylic acid
Reaction equation
C[O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([O:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:31])[C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=3)=[CH:17][N:16]=1)=[CH:9][CH:8]=2)=[O:4].[OH-].[Na+].O.Cl>C1COCC1.[Cl-].[Na+].O>[Cl:30][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][C:26]=1[Cl:29])[C:22]([NH:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][C:10]2[CH:11]=[C:12]3[C:7](=[CH:8][CH:9]=2)[NH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:13]3)=[N:16][CH:17]=1)=[O:31]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
5-[5-(3,4-Dichlorobenzoylamino)pyridin-2-yloxy]-1H-indole-2-carboxylic acid methyl ester (1.00 g, 2.19 mmol) was dissolved in THF (30 mL). To the solution were added 1 M sodium hydroxide (3.50 mL, 3.50 mmol) and water (15 ml), and the resulting solution was refluxed for 3 hours. After cooling with ice, 1 M hydrochloric acid (3.50 mL, 3.50 mmol) and brine (50 mL) was added to the reaction solution, and the mixture was extracted with ethyl acetate (30 ml). After the organic layer was washed with brine, then dried over anhydrous sodium sulfate, the solvent was evaporated. The obtained residue was crystallized from n-hexane to yield 0.875 g of the title compound as a pale yellow powder.
Workup
- temperaturethe resulting solution was refluxed for 3 hours
- additionwas added to the reaction solution
- extractionthe mixture was extracted with ethyl acetate (30 ml)
- washAfter the organic layer was washed with brine
- dry with materialdried over anhydrous sodium sulfate
- customthe solvent was evaporated
- customThe obtained residue was crystallized from n-hexane
Sources & evidence
- ORD record
- ord-d4437ba8ce71437c89ff2d98acb0d434
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08551999B2
Reaction notes
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