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

Dimethylformamide → 2-Benzyl-7-cyano-3-hydroxyquinoline

HRID 1359420
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1359420
[CH2:1]([C:8]1[C:17]([OH:18])=[CH:16][C:15]2[C:10](=[CH:11][C:12](Br)=[CH:13][CH:14]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][N:21](C)C=O>[C-]#N.[Zn+2].[C-]#N.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([C:8]1[C:17]([OH:18])=[CH:16][C:15]2[C:10](=[CH:11][C:12]([C:20]#[N:21])=[CH:13][CH:14]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 6228DimethylformamideHCID 181822012-Benzyl-7-bromo-3-hydroxyquinoline

Produkt 1

HCID 181822382-Benzyl-7-cyano-3-hydroxyquinoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysator

Versuchsvorschrift

A mixture of 370 mg of 2-benzyl-7-bromo-3-hydroxyquinoline (including n-hexadecyl-tri-n-butylphosphonium bromide), 208 mg of zinc cyanide, 272 mg of tetrakis(triphenylphosphine) palladium(0) and 10 ml of N,N-dimethylformamide was heated under stirring for 7 hours in an oil bath kept at 90° C. After cooling as it was, insoluble matters were filtered through Celite and an aqueous potassium carbonate solution was added to the filtrate. The mixture was extracted with ethyl acetate, and the organic phase was washed with brine and the solvent was removed. The residue was subjected to silica gel column chromatography and eluted with hexane/ethyl acetate (3:1) and then with hexane/ethyl acetate (2:1), to give 203 mg of the target compound.

Aufarbeitung

  1. temperaturewas heated
  2. customkept at 90° C
  3. temperatureAfter cooling as it
  4. filtrationinsoluble matters were filtered through Celite
  5. additionan aqueous potassium carbonate solution was added to the filtrate
  6. extractionThe mixture was extracted with ethyl acetate
  7. washthe organic phase was washed with brine
  8. customthe solvent was removed
  9. washeluted with hexane/ethyl acetate (3:1)

Quellen und Nachweise

ORD-Eintrag
ord-60c997e5a1c4431bb657eb2d6e0d71e5
Quelldatensatz
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06599917B1

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion