Diethyl Malonate → Ethyl 6-bromo-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate

HRID 1362308Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1362308
[NH2:1][C:2]1[C:7]([CH:8]=O)=[CH:6][C:5]([Br:10])=[CH:4][N:3]=1.[C:11](OCC)(=[O:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].N1CCCCC1>CCO>[CH2:16]([O:15][C:13]([C:12]1[C:11](=[O:18])[NH:1][C:2]2[C:7]([CH:8]=1)=[CH:6][C:5]([Br:10])=[CH:4][N:3]=2)=[O:14])[CH3:17]

Komponenten

5

Edukt 3

HCID 7761Diethyl MalonateHCID 8082PiperidineHCID 242137922-Amino-5-bromo-3-pyridinecarbaldehyde

Produkt 1

HCID 53396436Ethyl 6-bromo-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylateAusbeute 57,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 2-amino-5-bromo-pyridine-3-carbaldehyde (4.00 g, 14.2 mmol), diethyl malonate (21.6 mL, 142 mmol) and piperidine (7.00 mL, 71.0 mmol) in EtOH (70 mL) was heated to reflux overnight. The mixture was cooled to room temperature and the solid was collected by filtration to give the title compound (2.41 g, 57%) as an off-white solid: 1H NMR (300 MHz, CDCl3) δ 12.65 (s, 1H), 8.70 (d, J=2.4 Hz, 1H), 8.56 (d, J=2.4 Hz, 1H), 8.45 (s, 1H), 4.29 (q, J=7.1 Hz, 2H), 1.30 (t, J=7.1 Hz, 3H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. filtrationthe solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-1e972c7186354cd485e2c54c55fe2396
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879872B2

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