Potassium Hydroxide → 4-(2-carboxyethyl)-3-methyl-5-(5-methyl-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-1H-pyrrole-2-carboxylic acid

HRID 24546

Reaktionsgleichung

C([O:3][C:4]([C:6]1[NH:7][C:8]([CH:19]=O)=[C:9]([CH2:12][CH2:13][C:14]([O:16]CC)=[O:15])[C:10]=1[CH3:11])=[O:5])C.[CH3:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[NH:27][C:26](=[O:31])[CH2:25]2.[OH-].[K+]>N1CCCCC1.C(O)C>[C:14]([CH2:13][CH2:12][C:9]1[C:10]([CH3:11])=[C:6]([C:4]([OH:3])=[O:5])[NH:7][C:8]=1[CH:19]=[C:25]1[C:24]2[C:28](=[CH:29][CH:30]=[C:22]([CH3:21])[CH:23]=2)[NH:27][C:26]1=[O:31])([OH:16])=[O:15]

Komponenten

Reaktionsbedingungen

Temperatur: 95 °C

Versuchsvorschrift

5-Formyl-4-(2-ethoxycarbonylethyl)-3-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (560 mg), 5-methyl-2-oxindole (300 mg), and piperidine (4 drops) in ethanol (4 mL) were stirred at 90° C. for 2 hours. Potassium hydroxide (537 mg) was added to the mixture and it was then stirred at 95° C. for an additional hour. The reaction mixture was cooled and concentrated. The residue was dissolved into 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 496 mg of 4-(2-carboxyethyl)-3-methyl-5-(5-methyl -2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-1H-pyrrole-2-carboxylic acid.

Aufarbeitung

temperatureThe reaction mixture was cooled
concentrationconcentrated
dissolutionThe residue was dissolved into water
filtrationThe precipitate was filtered
washwashed with water
customdried in a vacuum oven overnight

Quellen und Nachweise

ORD-Eintrag: ord-1237e8f3e5a440aba7ea0153fc43cc5c
Quelldatensatz: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06855730B2

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