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

Cesium carbonate → 3-Nitro-5-(2-oxopyrrolidin-1-yl)benzoic acid

HRID 852666
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 852666
Br[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6].[C:14]([O-:17])([O-])=O.[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.O1CCOCC1>[N+:11]([C:9]1[CH:8]=[C:4]([CH:3]=[C:2]([N:11]2[CH2:9][CH2:8][CH2:4][C:14]2=[O:17])[CH:10]=1)[C:5]([OH:7])=[O:6])([O-:13])=[O:12]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 10796Cesium carbonateHCID 2393363-Bromo-5-nitrobenzoic acid

Produkt 1

HCID 222530233-Nitro-5-(2-oxopyrrolidin-1-yl)benzoic acidAusbeute 148,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)Katalysator
HCID 9811564
Bis(dibenzylideneacetone)palladium
Katalysator
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A flask was charged under nitrogen with 3-bromo-5-nitro-benzoic acid (D5) (12.3 g, 50 mmol, 1 equiv), Cs2CO3 (24.4 g, 75 mmol, 1.5 equiv), tris(dibenzylideneacetone)dipalladium(0) (229 mg, 0.25 mmol, 0.005 equiv), Xantphos (433 mg, 0.75 mmol, 0.015 equiv) and dioxan (120 ml). 2-Pyrrolidin-2-one (5.7 ml, 75 mmol, 1.5 equiv) was then added via syringe and the resulting mixture was stirred at reflux for 60 h then cooled to room temperature and concentrated in vacuo. The residue was diluted with H2O and 1N aqueous NaOH solution and extracted twice with Et2O. The aqueous phase was then acidified to pH 1 and extracted three times with AcOEt. The combined organic phases were dried over MgSO4 and concentrated in vacuo to give 3-nitro-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid (A27) (9.3 g, 75%) as a pale brown solid.

Aufarbeitung

  1. temperatureat reflux for 60 h
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with H2O and 1N aqueous NaOH solution
  4. extractionextracted twice with Et2O
  5. extractionextracted three times with AcOEt
  6. dry with materialThe combined organic phases were dried over MgSO4
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6cebce2ac16e40bd8e118f207827b04f
Quelldatensatz
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07253198B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion