Hydrochloric Acid → Ethyl 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate

HRID 6692

Reaktionsgleichung

Reaktionsgleichung von HRID 6692
C([C:3](CC)([C:7]([O-:9])=[O:8])C([O-])=O)C.[H-].[Na+].[H][H].[C:16]12[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=1)[NH:21][C:20](=[O:27])[O:19][C:17]2=O.Cl.[CH3:29][C:30](N(C)C)=O>>[CH2:29]([O:9][C:7]([C:3]1[C:20](=[O:27])[NH:21][C:22]2[C:16]([C:17]=1[OH:19])=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:8])[CH3:30]

Komponenten

7

Edukt 6

HCID 313Hydrochloric AcidHCID 8359Isatoic AnhydrideHCID 24758Sodium hydrideHCID 31374Dimethylacetamide2×HCID 69515632,2-DiethylpropanedioateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 54684458Ethyl 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylateAusbeute 47 %

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A solution of diethylmalonate (80 g, 0.50 mol) was added slowly to a suspension of sodium hydride (60% in mineral oil, 22 g, 0.55 mol) in dimethylacetamide under N2 atmosphere. The mixture was allowed to stir at room temperature until the evolution of hydrogen gas ceased, then heated to 90° C. for 30 min. and cooled to room temperature. A solution of isatoic anhydride (89.72 g, 0.55 mmol) in dimethylacetamide was added slowly and heated at 120° C. for 15 h. The mixture was cooled to room temperature, poured into ice water and acidified by cold 10% HCl. The solids formed were filtered and washed several times by water to yield 55 g (47%) of white solids. Mp 173° C. 1H NMR (DMSO-d6): δ 1.30 (t, J=6.9 Hz, 3H), 4.33 (q, J=6.9 Hz, 2H), 7.18 (t, J=7.5 Hz, 1H), 7.26 (d, J=8.2 Hz, 1H), 7.62 (t, J=7.2 Hz, 1H), 7.93 (d, J=8.0 Hz, 1H) 11.50 (s, 1H), 13.5 (s, 1H). EIMS m/z 234 (M+1), 256 (M+23). Anal. (C12H11NO4) C, H, N.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. temperatureheated at 120° C. for 15 h
  3. temperatureThe mixture was cooled to room temperature
  4. customThe solids formed
  5. filtrationwere filtered
  6. washwashed several times by water

Quellen und Nachweise

ORD-Eintrag
ord-5e984f0bb90a49f49c73a342593a21ea
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084141B2

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