Propylamine → ethyl (2Z)-3-(2-chloropyridin-3-yl)-2-cyano-3-(propylamino)acrylate

HRID 444695Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 444695
Cl[C:2]([C:11]1[C:12]([Cl:17])=[N:13][CH:14]=[CH:15][CH:16]=1)=[C:3]([C:9]#[N:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:18]([NH2:21])[CH2:19][CH3:20]>O1CCCC1>[Cl:17][C:12]1[C:11](/[C:2](/[NH:21][CH2:18][CH2:19][CH3:20])=[C:3](\[C:9]#[N:10])/[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:16][CH:15]=[CH:14][N:13]=1

Komponenten

4

Edukt 2

HCID 7852PropylamineHCID 86654759Ethyl 3-chloro-3-(2-chloropyridin-3-yl)-2-cyanoacrylate

Produkt 1

HCID 58319383ethyl (2Z)-3-(2-chloropyridin-3-yl)-2-cyano-3-(propylamino)acrylateAusbeute 74,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of ethyl 3-chloro-3-(2-chloropyridin-3-yl)-2-cyanoacrylate (0.3 g, 1.10 mmol, 1 eq.) in 5 ml of tetrahydrofuran was added propylamine (0.131 g, 2.21 mmol, 2 eq.) at room temperature. After being stirred for 8 h at 80° C., the mixture was evaporated. The residue was diluted with AcOEt and the precipitate was filtered off. The filtrate was evaporated and the residual oil was subjected to column chromatography to give ethyl (2Z)-3-(2-chloropyridin-3-yl)-2-cyano-3-(propylamino)acrylate (0.240 g, 74% yield).

Aufarbeitung

  1. customthe mixture was evaporated
  2. additionThe residue was diluted with AcOEt
  3. filtrationthe precipitate was filtered off
  4. customThe filtrate was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-e5f3d28943ad4489abf51a9845c02846
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476197B2

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