Dimethylformamide → Ethyl 2-(6-cyano-2-oxoquinolin-1(2h)-yl)acetate

HRID 2098055

Reaktionsgleichung

Reaktionsgleichung von HRID 2098055
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:7](=[O:18])[CH:6]=[CH:5]2.C(OCC)(=O)C.[CH3:25][N:26](C)C=O>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:25]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:7](=[O:18])[CH:6]=[CH:5]2)#[N:26]

Komponenten

6

Edukt 3

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 68786198ethyl 2-(6-bromo-2-oxoquinolin-1(2H)-yl)acetate

Produkt 1

HCID 68786957Ethyl 2-(6-cyano-2-oxoquinolin-1(2h)-yl)acetateAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

Ethyl 2-(6-bromo-2-oxoquinolin-1(2H)-yl)acetate (2.37 g, 7.64 mmol)cuprous cyanide (8.87 g, 99.0 mmol), and tetrakis(triphenylphosphine)palladium(0) (3.50 g, 3.03 mmol) in dimethylforamide (100 ml) was placed into a preheated oil bath at 140° C. After stirring for 24 h, the solution was diluted with water and extracted with ethyl acetate. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was flash chromatographed with 9:1, 4:1, 7:3, and 3:2 methylene chloride:ethyl acetate as the eluant to afford 0.74 g (38% yield) of ethyl 2-(6-cyano-2-oxoquinolin-1(2H)-yl)acetate. Method [7] retention time 2.87 min by HPLC (M+257).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customchromatographed with 9:1, 4:1, 7:3, and 3:2 methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-76581d33bd0c4795b9626d4cd5a88f36
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450363B2

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