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

Dichloromethane → 2-(4-Nitrophenyl)-4-quinolinecarboxylic acid methyl ester

HRID 1259861
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1259861
C(Cl)Cl.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[N+:12]([C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)([O-:14])=[O:13].[CH3:24][O:25][C:26]([C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]=[C:30](Cl)[CH:29]=1)=[O:27]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CN(C=O)C.O1CCOCC1>[CH3:24][O:25][C:26]([C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]=[C:30]([C:18]2[CH:19]=[CH:20][C:15]([N+:12]([O-:14])=[O:13])=[CH:16][CH:17]=2)[CH:29]=1)=[O:27]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 27735524-Nitrophenylboronic acidHCID 5202936Methyl 2-chloroquinoline-4-carboxylate

Produkt 1

HCID 34203702-(4-Nitrophenyl)-4-quinolinecarboxylic acid methyl esterAusbeute 78,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Katalysator
HCID 6228DimethylformamideLösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

PdCl2(dppf).CH2Cl2 (184 mg, 0.23 mmol), tripotassium phosphate (624 mg, 4.51 mmol), and 4-nitrophenylboronic acid (958 mg, 4.51 mmol) were added to a 1,4-dioxane (5 mL)/DMF (1 mL) mixed solution of 2-chloro-4-quinolinecarboxylic acid methyl ester (500 mg, 2.26 mmol) obtained in Reference Example 3, and the mixture was heated with stirring overnight at 85° C. in an argon atmosphere. After the reaction solution was concentrated, to the residue, a saturated aqueous solution of sodium chloride and methylene chloride were added, and insoluble matter was filtered off through celite. After that, the residue was subjected to extraction with methylene chloride and dried over anhydrous sodium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography to obtain 2-(4-nitrophenyl)-4-quinolinecarboxylic acid methyl ester (549 mg, 1.78 mmol).

Aufarbeitung

  1. customobtained in Reference Example 3
  2. temperaturethe mixture was heated
  3. concentrationAfter the reaction solution was concentrated, to the residue
  4. additiona saturated aqueous solution of sodium chloride and methylene chloride were added
  5. filtrationinsoluble matter was filtered off through celite
  6. extractionAfter that, the residue was subjected to extraction with methylene chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off
  9. customthe obtained residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-eee545d12a32431c9e711717562ac72d
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08466290B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion