Hydrochloric Acid → 4-(2-carboxyethyl)-3-methyl-5-(5-chloro-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-1H-pyrrole-2-carboxylic acid
Reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]([CH:19]=[C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([Cl:29])[CH:27]=3)[NH:22][C:21]2=[O:30])=[C:9]([CH2:12][CH2:13][C:14]([O:16]CC)=[O:15])[C:10]=1[CH3:11])=[O:5])C.[OH-].[K+].Cl>C(O)C.O>[C:14]([CH2:13][CH2:12][C:9]1[C:10]([CH3:11])=[C:6]([C:4]([OH:5])=[O:3])[NH:7][C:8]=1[CH:19]=[C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([Cl:29])[CH:27]=2)[NH:22][C:21]1=[O:30])([OH:16])=[O:15]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 95 °C
Procedure
A mixture of 4-(2-ethoxycarbonylethyl)-3-methyl-5-(5-chloro-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-1H-pyrrole-2-carboxylic acid ethyl ester (346 mg) and potassium hydroxide (560 mg) in ethanol (5 mL) was heated to 95° C. and then cooled, upon which red crystals formed. The crystals were dissolved in water and acidified with 2 N hydrochloric acid to pH 2. The precipitate was filtered, washed with water, and dried in a vacuum oven overnight to give 299 mg (100%) of 4-(2-carboxyethyl)-3-methyl-5-(5-chloro-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-1H-pyrrole-2-carboxylic acid as a brown solid.
Workup
- temperaturecooled, upon which red crystals
- customformed
- filtrationThe precipitate was filtered
- washwashed with water
- customdried in a vacuum oven overnight
Sources & evidence
- ORD record
- ord-4fb07d448c45448ba36c0981db42ab3f
- Source dataset
- uspto-grants-2003_03
- Patent number
- US06531502B1
Reaction notes
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