Hydrochloric Acid → 4-Hydroxy-1-methyl-3-nitro-1,2-dihydroquinolin-2-one

HRID 6688

Reaktionsgleichung

Reaktionsgleichung von HRID 6688
C(O[C:4](=[O:9])[CH2:5][N+:6]([O-:8])=[O:7])C.[H-].[Na+].[H][H].[CH3:14][N:15]1C(=O)O[C:18](=[O:19])[C:17]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:16]12.Cl>CC(N(C)C)=O>[OH:19][C:18]1[C:17]2[C:16](=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:15]([CH3:14])[C:4](=[O:9])[C:5]=1[N+:6]([O-:8])=[O:7]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 25160N-Methylisatoic anhydrideHCID 69379Ethyl nitroacetateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 546821234-Hydroxy-1-methyl-3-nitro-1,2-dihydroquinolin-2-oneAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A solution of ethylnitroacetate (15.96 g, 120 mmol) was added slowly in a suspension of sodium hydride (60% in mineral oil, 5.28 g, 132 mmol) 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 N-methylisatoic anhydride (23.38 g, 132 mmol) in dimethylacetamide was added slowly and heated overnight at 120° C. 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 7.1 g (27%) of yellow solids. Mp 193° C. 1H NMR (DMSO-d6): δ 3.60 (s, 3H), 7.37 (t, J=7.6 Hz, 1H), 7.58 (d, J=8.5 Hz, 1H), 7.77 (t, J=7.5 Hz, 1H), 8.12 (d, J=7.9 Hz, 1H). EIMS m/z 221 (M+1), 243 (M+23). Anal. (C10H8N2O4) C, H, N.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. temperatureheated overnight at 120° C
  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-a34b72d6641642e8a67a6948726a049e
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084141B2

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