Dimethylformamide → 3-Benzyl-7-chloroquinoline-2-carbaldehyde

HRID 271831Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 271831
[CH2:1]([C:8]1[C:9](I)=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[C:13]([Cl:18])[CH:12]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Mg]Cl)(C)C.CN([CH:28]=[O:29])C>C1COCC1>[CH2:1]([C:8]1[C:9]([CH:28]=[O:29])=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[C:13]([Cl:18])[CH:12]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 598361993-Benzyl-7-chloro-2 iodo-quinolineHCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 598361973-Benzyl-7-chloroquinoline-2-carbaldehydeAusbeute 110,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 3-benzyl-7-chloro-2 iodo-quinoline (1.5 g, 3.95 mmol) in 15 mL of anhydrous THF at −78° C., was added isopropylmagnesium chloride (5.93 ml, 11.85 mmol). After stirring at −78° C. for 30 minutes, DMF (1.53 ml, 19.8 mmol) was added. The reaction mixture was allowed to slowly warm to ambient temperature over two hours. It was then quenched with saturated NH4Cl and extracted with ethyl acetate (3×). The combined organic layers were washed with brine, dried over MgSO4, and the solvent was removed in vacuo yielding 1.23 g of 3-benzyl-7-chloroquinoline-2-carbaldehyde 24 as brown oil.

Aufarbeitung

  1. temperatureto slowly warm to ambient temperature over two hours
  2. customIt was then quenched with saturated NH4Cl
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bedbda194ea4456c94770f40febc4c85
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452996B2

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