Ethyl 5,7-diethyl-4-hydroxy-2-oxo-1,2-dihydro-1,6-naphthyridine-3-carboxylate → 5,7-diethyl-4-hydroxy-1,6-naphthyridin-2(1H)-one

HRID 487383Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 487383
[CH2:1]([C:3]1[N:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[C:5]([OH:21])=[C:6](C(OCC)=O)[C:7](=[O:15])[NH:8]2)[CH3:2]>O.O1CCOCC1.Cl>[CH2:1]([C:3]1[N:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[C:5]([OH:21])=[CH:6][C:7](=[O:15])[NH:8]2)[CH3:2]

Komponenten

5

Edukt 1

HCID 54684680Ethyl 5,7-diethyl-4-hydroxy-2-oxo-1,2-dihydro-1,6-naphthyridine-3-carboxylate

Produkt 1

HCID 546846815,7-diethyl-4-hydroxy-1,6-naphthyridin-2(1H)-oneAusbeute 55,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Compound B (1 g) was dissolved in a mixture of water (1 ml), 1,4-dioxan (2 ml) and concentrated hydrochloric acid (1 ml) and the mixture was heated at reflux for 3 hours. The reaction mixture was then cooled and the suspended solid was collected by filtration. The solid was washed with ethanol and ether and dried under vacuum to give 5,7-diethyl-4-hydroxy-1,6-naphthyridin-2(1H)-one (C) (0.42 g), m.p. 322°-325° C.; NMR (d6 -DMSO): 1.3(dt, 6H), 2.99(q, 2H), 3.47(q, 2H), 6.0(s, 1H), 7.28(s, 1H), 12.3(s, 1H); mass spectrum (CI, ammonia): 219 (M+H)+ ; microanalysis, found: C, 55.7; H, 5.9; N, 10.5%; C12H14N2O2.HCl.0.25H2O requires: C, 55.6; H, 5.6; N, 10.8%.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3 hours
  3. temperatureThe reaction mixture was then cooled
  4. filtrationthe suspended solid was collected by filtration
  5. washThe solid was washed with ethanol and ether
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-32ec258398e244f89cb828ac326830b0
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05294620

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