Ammonium Chloride → 1-(Quinolin-6-yl)ethan-1-one

HRID 16023

Reaktionsgleichung

Reaktionsgleichung von HRID 16023
CON(C)[C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][CH:10]=[CH:9]2)=[O:5].[CH3:17][Mg+].[Br-].[NH4+].[Cl-]>C1COCC1>[N:12]1[C:13]2[C:8](=[CH:7][C:6]([C:4](=[O:5])[CH3:17])=[CH:15][CH:14]=2)[CH:9]=[CH:10][CH:11]=1

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 55211172N-Methoxy-N-methylquinoline-6-carboxamideHCID 178418689HCID 178418689, Verbindung

Produkt 1

HCID 2585591-(Quinolin-6-yl)ethan-1-oneAusbeute 97,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of quinoline-6-carboxylic acid methoxy-methyl-amide (11.97 g, 55.35 mmol) in anhydrous THF (200 mL) was added MeMgBr (1.5 M in THF, 55 mL, 83 mmol) at 0° C. under nitrogen. The reaction was allowed to warm to ambient temperature over 16 hours. Sat. NH4Cl (20 mL) was added to quench the reaction. The reaction solution was then extracted with EtOAc (3×50 mL). The combined organics were dried over Na2SO4, filtered, and concentrated to give 1-quinolin-6-yl-ethanone (9.2 g, 97% yield).

Aufarbeitung

  1. customto quench
  2. customthe reaction
  3. extractionThe reaction solution was then extracted with EtOAc (3×50 mL)
  4. dry with materialThe combined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1b533ba8a3a34f338769c7d82baef3e5
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732604B2

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