Water → 2-Oxo-1-phenyl-1,2-dihydro-1,8-naphthyridine-3-carboxylic acid

HRID 2194528Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2194528
[O:1]=[C:2]1[C:11]([C:12]([O:14]CC)=[O:13])=[CH:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1>[O:1]=[C:2]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 67010579Ethyl 1,2-dihydro-2-oxo-1-phenyl-1,8-naphthyridine-3-carboxylate

Produkt 1

HCID 534020662-Oxo-1-phenyl-1,2-dihydro-1,8-naphthyridine-3-carboxylic acidAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

2.00 g (6.8 mmol) of ethyl 2-oxo-1-phenyl-1,2-dihydro-1,8-naphthyridine-3-carboxylate was dissolved in 1,4-dioxane (100 mL), and 1.41 g (10.2 mmol) of potassium carbonate and 200 mL of water were added thereto at room temperature. The resulting mixture was stirred for 3 hours at 50° C. The solvent was distilled off under reduced pressure from the reaction mixture, and the residue was dissolved in water. Concentrated hydrochloric acid was added thereto to make the solution acidic. A solid precipitated therefrom was separated by filtration, and was dried. Thus, 1.72 g of the title compound was obtained as pale yellow crystals (yield: 95%).

Aufarbeitung

  1. customat room temperature
  2. distillationThe solvent was distilled off under reduced pressure from the reaction mixture
  3. dissolutionthe residue was dissolved in water
  4. additionConcentrated hydrochloric acid was added
  5. customA solid precipitated
  6. customtherefrom was separated by filtration
  7. customwas dried

Quellen und Nachweise

ORD-Eintrag
ord-37d1196e022f42c68aace7823433f02f
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08334236B2

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