Diethyl Malonate → Ethyl 1,2-dihydro-2-oxo-1-phenyl-1,8-naphthyridine-3-carboxylate

HRID 2194527Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2194527
[C:1]1([NH:7][C:8]2[N:15]=[CH:14][CH:13]=[CH:12][C:9]=2[CH:10]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16](OCC)(=[O:23])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].N1CCCCC1>C(O)C>[O:23]=[C:16]1[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:10][C:9]2[C:8](=[N:15][CH:14]=[CH:13][CH:12]=2)[N:7]1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 7761Diethyl MalonateHCID 8082PiperidineHCID 13983610HCID 13983610, Verbindung

Produkt 1

HCID 67010579Ethyl 1,2-dihydro-2-oxo-1-phenyl-1,8-naphthyridine-3-carboxylateAusbeute 79,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

6.28 g (31.7 mmol) of 2-(phenylamino)nicotinaldehyde was dissolved in ethanol (150 mL), and 7.62 g (47.6 mmol) of diethyl malonate and 1.35 g (15.9 mmol) of piperidine were added thereto. The resulting mixture was stirred overnight at 100° C. The reaction mixture was cooled, and a solid precipitated thereby was separated by filtration. The solid was washed sequentially with ethanol and diisopropyl ether. Thus, 7.42 g of the title compound was obtained as a pale yellow solid (yield: 800).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. customa solid precipitated
  3. customthereby was separated by filtration
  4. washThe solid was washed sequentially with ethanol and diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-96944cf5db6744d3bc7dda3345aeedff
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08334236B2

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