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Ethanol → 6-(piperazin-1-yl)-3,4-dihydroquinolin-2(1H)-one

HRID 1649246
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1649246
Cl.[N+:2]([C:5]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[CH:14][C:6]=1[CH:7]=[CH:8][C:9](OCC)=[O:10])([O-])=O.C(O)C.[OH-].[Na+]>[Ni].O>[N:18]1([C:15]2[CH:14]=[C:6]3[C:5](=[CH:17][CH:16]=2)[NH:2][C:9](=[O:10])[CH2:8][CH2:7]3)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 705346722-Nitro-5-piperazinylcinnamic acid ethyl ester hydrochloride

Produkt 1

HCID 111178966-(piperazin-1-yl)-3,4-dihydroquinolin-2(1H)-oneAusbeute 54,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysator
HCID 962
Water
Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Ethyl 2-nitro-5-piperazinylcinnamate hydrochloride (3.5 g) was dissolved in a mixed solvent consisting of 150 ml of ethanol and 45 ml of water and the solution was adjusted to pH of about 7 with an aqueous sodium hydroxide. The solution was added 2 g of Raney nickel catalyst and placed in a glass autoclave followed by stirring at 80° C. under hydrogen gas pressure of 5 kg/cm2 for 4 hours. After removing hydrogen gas the reaction mixture was taken out and the catalyst was removed. The solution was concentrated to dryness and methanol was added to the residue to precipitate crystals, which then were collected by filtration and recrystallized from methanol to give 1.3 g of 6-(1-piperazinyl)-3,4-dihydrocarbostyril, m.p. 224°-231.5° C.

Aufarbeitung

  1. customAfter removing hydrogen gas the reaction mixture
  2. customthe catalyst was removed
  3. concentrationThe solution was concentrated to dryness and methanol
  4. additionwas added to the residue
  5. customto precipitate crystals, which
  6. filtrationthen were collected by filtration
  7. customrecrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-4a0ed36b73494479b7464c1071d00e34
Quelldatensatz
uspto-grants-1983_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04415572

Notizen zur Reaktion

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