Hydrochloric Acid → 1-benzyl-3-ethoxycarbonyl-4-hydroxy-6-methyl-2(1H)-quinolinone

HRID 1767473Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1767473
[C:1]([O:9]CC)(=O)[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[H][H].[CH2:16]([N:23]1[C:28]2[CH:29]=[CH:30][C:31]([CH3:33])=[CH:32][C:27]=2[C:26](=O)[O:25]C1=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl>CC(N(C)C)=O>[CH2:6]([O:5][C:3]([C:2]1[C:1](=[O:9])[N:23]([CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:28]2[C:27]([C:26]=1[OH:25])=[CH:32][C:31]([CH3:33])=[CH:30][CH:29]=2)=[O:4])[CH3:7]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 210819161-Benzyl-6-methyl-1H-benzo[d][1,3]oxazine-2,4-dioneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 547306581-benzyl-3-ethoxycarbonyl-4-hydroxy-6-methyl-2(1H)-quinolinoneAusbeute 97,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Neat diethyl malonate (19.07 mL, 125 mmol) was added slowly to a suspension of sodium hydride (60% in mineral oil, 5.52 g, 138 mmol) in dimethylacetamide under N2 atmosphere. The mixture was stirred 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 Compound 12 (36.8 g, 138 mmol) in dimethylacetamide was added slowly and the mixture was heated overnight at 110° C. The mixture was cooled to room temperature, poured into ice water, and acidified by cold 10% HCl. The solids formed were filtered, washed several times by water, and dried at room temperature under vacuum to yield 41 g (97%) of white solids. M.P. 113° C. 1H NMR (DMSO-d6): δ 1.31 (t, J=7.5 Hz, 3H), 2.33 (s, 3H), 4.35 (q, J=7.5 Hz, 2H), 5.43 (s, 2H), 7.15–7.30 (m, 6H), 7.43 (dd, J=1.6, 8.7 Hz, 1H), 7.85 (d, J=1.5 Hz, 1H). EIMS m/z 338 (M+1), 360 (M+23). Anal. (C20H19NO4) C, H, N.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. temperaturethe mixture was heated overnight at 110° C
  3. temperatureThe mixture was cooled to room temperature
  4. customThe solids formed
  5. filtrationwere filtered
  6. washwashed several times by water
  7. customdried at room temperature under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f0cb0813474142d6812076b4c3e19f92
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07235546B2

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