N,N-Dimethylaniline → 6-Chloro-1-cycloprop yl-carbonyl-4-oxo-1,2,3,4-tetrahydroquinoline

HRID 653119Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 653119
C1([C:4](Cl)=[O:5])CC1.[Cl:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH2:13][CH2:12][C:11]2=[O:18].CN(C)[C:21]1[CH:26]=[CH:25]C=CC=1>C(Cl)(Cl)Cl.CN(C)C1C=CN=CC=1>[Cl:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH:25]1[CH2:26][CH2:21]1)[C:13](=[C:4]=[O:5])[CH2:12][C:11]2=[O:18]

Komponenten

6

Edukt 3

HCID 949N,N-DimethylanilineHCID 77637Cyclopropanecarbonyl chlorideHCID 124791046-Chloro-2,3-dihydroquinolin-4(1H)-one

Produkt 1

HCID 867416286-Chloro-1-cycloprop yl-carbonyl-4-oxo-1,2,3,4-tetrahydroquinolineAusbeute 86,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

A solution of cyclopropyl-carbonyl chloride (2.09 g) in chloroform (5 ml) was added dropwise to a solution of 6-chloro-4-oxo-1,2,3,4-tetrahydroquinoline (1.815 g), N,N-dimethylaniline (2.42 g), and 4-dimethylaminopyridine (0.488 g) in chloroform (15 ml) with stirring and ice cooling over a period of 10 minutes. After being stirred overnight at ambient temperature, the mixture was washed successively with 10% hydrochloric acid, water, aqueous sodium bicarbonate, and water, dried over magnesium sulfate, and evaporated in vacuo. The residual solid was washed with diethyl ether and dried to give 6-chloro-1-cyclopropyl-carbonyl-4-oxo-1,2,3,4-tetrahydroquinoline (2.14 g).

Aufarbeitung

  1. stirringAfter being stirred overnight at ambient temperature
  2. washthe mixture was washed successively with 10% hydrochloric acid, water, aqueous sodium bicarbonate, and water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. washThe residual solid was washed with diethyl ether
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-e478162fa4754bcf9267e7a1f02e53a1
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04675324

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