Ethanone, 1-(2-amino-4,5-dimethoxyphenyl)- → HCID 178419049, Verbindung

HRID 7464

Reaktionsgleichung

Reaktionsgleichung von HRID 7464
[N:1]([O-])=O.[Na+].[CH3:5][C:6]([C:8]1[C:13]([NH2:14])=[CH:12][C:11]([O:15][CH3:16])=[C:10]([O:17][CH3:18])[CH:9]=1)=[O:7]>C(O)(=O)C.S(=O)(=O)(O)O>[OH:7][C:6]1[C:8]2[C:13](=[CH:12][C:11]([O:15][CH3:16])=[C:10]([O:17][CH3:18])[CH:9]=2)[N:14]=[N:1][CH:5]=1

Komponenten

5

Edukt 2

HCID 602085Ethanone, 1-(2-amino-4,5-dimethoxyphenyl)-HCID 23668193Sodium Nitrite

Produkt 1

HCID 178419049HCID 178419049, VerbindungAusbeute 87,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

The starting material, 4-hydroxy-6,7-dimethoxycinnoline was obtained by adding a solution of sodium nitrite (1.9 g, 27 mmol) to a solution of 2-amino-4,5-dimethoxyacetophenone (5 g, 0.025 mol) in acetic acid (90 ml) and sulphuric acid (15 ml) at a rate to maintain the temperature below 20° C. The mixture was heated at 80° C. for 90 minutes. After cooling and concentrating the solution to half its original volume, the residue was poured into ether (800 ml). The solid was collected by filtration and suspended in water (200 ml). After adjusting to pH7 with sodium hydroxide the solid was filtered, washed with water, methanol and methylene chloride to give 4-hydroxy-6,7-dimethoxycinnoline (4.5 g, 87%).

Aufarbeitung

  1. temperatureto maintain the temperature below 20° C
  2. temperatureAfter cooling
  3. concentrationconcentrating the solution to half its original volume
  4. additionthe residue was poured into ether (800 ml)
  5. filtrationThe solid was collected by filtration
  6. filtrationwas filtered
  7. washwashed with water, methanol and methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-a0ab3c0fa52b4471a489048eafec37c1
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087602B2

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