StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Pyridine → acetic acid (2-oxo-2,3-dihydro-1H-indol-5-ylcarbamoyl)-methyl ester

HRID 2191474
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2191474
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.N1C=CC=CC=1.Cl[C:19]([CH2:21][O:22][C:23](=[O:25])[CH3:24])=[O:20]>ClCCl>[O:11]=[C:6]1[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[C:2]([NH:1][C:19]([CH2:21][O:22][C:23](=[O:25])[CH3:24])=[O:20])[CH:3]=2)[NH:7]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 26297Acetoxyacetyl chlorideHCID 27732135-Amino-2-oxindole

Produkt 1

HCID 59250067acetic acid (2-oxo-2,3-dihydro-1H-indol-5-ylcarbamoyl)-methyl esterAusbeute 60,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

5-Amino-1,3-dihydro-indol-2-one 30c (500 mg, 3.38 mmol) was dissolved in 10 ml of dichloromethane under stirring at room temperature, and pyridine (470 μl, 5 mmol) was added to the solution at −40° C. in a dry ice-acetone bath. Acetic acid chlorocarbonylmethyl ester (473 mg, 3.48 mmol) was dissolved in 10 ml of dichloromethane, the resulting solution was added dropwise to the above reaction solution. Upon completion of the addition, the dry ice-acetone was removed, and the reaction mixture was allowed to warm up to room temperature and stirred overnight. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was filtered. The filter cake was washed with water (10 ml×3) and recrystallized to obtain the title compound acetic acid (2-oxo-2,3-dihydro-1H-indol-5-ylcarbamoyl)-methyl ester 44a (510 mg, yield 60.7%) as a yellow solid.

Aufarbeitung

  1. additionthe resulting solution was added dropwise to the above reaction solution
  2. additionUpon completion of the addition
  3. customthe dry ice-acetone was removed
  4. temperatureto warm up to room temperature
  5. stirringstirred overnight
  6. filtrationthe reaction mixture was filtered
  7. washThe filter cake was washed with water (10 ml×3)
  8. customrecrystallized

Quellen und Nachweise

ORD-Eintrag
ord-d73bd6fb13b84b12aaca5c589ef43384
Quelldatensatz
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08329682B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion