Acetic Acid → 3-[2-(5-methyl-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1H-indol-3-yl]-propionic acid

HRID 1860905

Reaktionsgleichung

Reaktionsgleichung von HRID 1860905
[CH:1]([C:3]1[NH:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:11]=1[CH2:12][CH2:13][C:14]([OH:16])=[O:15])=O.[CH3:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][C:22](=[O:27])[CH2:21]2.N1CCCCC1.C(O)(=O)C>C(O)C>[CH3:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][C:22](=[O:27])[C:21]2=[CH:1][C:3]1[NH:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:11]=1[CH2:12][CH2:13][C:14]([OH:16])=[O:15]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 53257165-Methylindolin-2-oneHCID 106090023-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)propionic acid

Produkt 1

HCID 697646923-[2-(5-methyl-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1H-indol-3-yl]-propionic acidAusbeute 81,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 3-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propionic acid (5.4 g), 3.2 g of 5-methyl-2-oxindole and 2.7 g of piperidine in 25 mL of ethanol was refluxed for 4 hours. Upon addition of acetic acid (8 mL), a precipitate formed. The mixture was refluxed for 5 minutes and cooled to ambient temperature. The precipitate was collected by vacuum filtration and washed with 20 mL of ethanol. The solids were slurry-washed with 30 mL of refluxing ethanol, cooled, collected by vacuum filtration, washed with 30 mL of ethanol and vacuum dried to give 6.2 g (80% yield) of 3-[2-(5-methyl-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1H-indol-3-yl]-propionic acid as an orange solid.

Aufarbeitung

  1. temperaturewas refluxed for 4 hours
  2. customa precipitate formed
  3. temperatureThe mixture was refluxed for 5 minutes
  4. filtrationThe precipitate was collected by vacuum filtration
  5. washwashed with 20 mL of ethanol
  6. washThe solids were slurry-washed with 30 mL of refluxing ethanol
  7. temperaturecooled
  8. filtrationcollected by vacuum filtration
  9. washwashed with 30 mL of ethanol and vacuum
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-2436fcfd2eeb4b8293e3ae45d8797a65
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06531502B1

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