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7-Methyl-1,8-naphthyridin-2-ol → 7-Methyl-3,4-dihydro-1,8-naphthyridin-2(1H)-one

HRID 1510697
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1510697
[CH3:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1>C(O)C.[C].[Pd]>[CH3:1][C:2]1[N:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 1

HCID 53736757-Methyl-1,8-naphthyridin-2-ol

Produkt 1

HCID 578152267-Methyl-3,4-dihydro-1,8-naphthyridin-2(1H)-oneAusbeute 45,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

A solution of 2.0 g of 7-methyl-1,8-naphthyridin-2(1H)-one in 150 mL of ethanol, 1.0 g of 5% palladium-carbon was added, and the mixture was stirred at 40 to 50° C. for 17 hours under a hydrogen atmosphere. The reaction mixture was cooled to room temperature, the insoluble substance was filtered off, and the filtration residue was washed with methanol. The solvent was distilled off under reduced pressure, and the resultant residue was purified by silica gel column chromatography using an eluent of hexane:ethyl acetate=1:1 to obtain 0.92 g of 7-methyl-3,4-dihydro-1,8-naphthyridin-2(1H)-one as a white solid.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe insoluble substance was filtered off
  3. washthe filtration residue was washed with methanol
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resultant residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d53bbc64350943309200f3b721896236
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08211908B2

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