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

HRID 24540Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 24540
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:30]=[CH:29][CH:28]=[C:27]2[C:23]=1[CH2:24][C:25](=[O:31])[NH:26]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:24]1[C:23]2[C:27](=[CH:28][CH:29]=[CH:30][C:22]=2[CH3:21])[NH:26][C:25]1=[O:31])([OH:16])=[O:15]

Komponenten

6

Edukt 3

HCID 14797Potassium HydroxideHCID 110223335-Formyl-4-(2-ethoxycarbonylethyl)-3-methyl-1H-pyrrole-2-carboxylic acid ethyl esterHCID 125793824-Methyl-1,3-dihydro-2H-indol-2-one

Produkt 1

HCID 542337294-(2-carboxyethyl)-3-methyl-5-(4-methyl-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-1H-pyrrole-2-carboxylic acidAusbeute 95,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8082PiperidineKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 5-formyl-4-(2-ethoxycarbonylethyl)-3-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (281 mg), 4-methyl-2-oxindole (147 mg) and piperidine (2 drops) in ethanol (2 mL) was stirred at 90° C. for 2 hours. Potassium hydroxide (213 mg) was added, the temperature was increased to 95° C. and held there for 1 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 337 mg (95%) of 4-(2-carboxyethyl)-3-methyl-5-(4-methyl-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-1H-pyrrole-2-carboxylic acid.

Aufarbeitung

  1. temperaturethe temperature was increased to 95° C.
  2. waitheld there for 1 hour
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved into water
  6. filtrationThe precipitate was filtered
  7. washwashed with water
  8. customdried in a vacuum oven overnight

Quellen und Nachweise

ORD-Eintrag
ord-bc13020b104d40ce800ed3388ae178bc
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855730B2

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