Sulfuric Acid → 7,8-Dimethoxy-2-methyl-3H-pyrimido[4,5-b]quinolin-4-one

HRID 1112259Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1112259
S(=O)(=O)(O)O.[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[N:14]=[C:13]([NH2:20])[C:12]([C:21]([NH2:23])=[O:22])=[CH:11]2.[C:24](OC(=O)C)(=O)[CH3:25].[OH-].[Na+]>O>[CH3:24][C:25]1[NH:23][C:21](=[O:22])[C:12]2[C:13]([N:20]=1)=[N:14][C:15]1[C:10]([CH:11]=2)=[CH:9][C:8]([O:7][CH3:6])=[C:17]([O:18][CH3:19])[CH:16]=1

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 7918Acetic Anhydride2×HCID 14798Sodium HydroxideHCID 7815842-Amino-6,7-dimethoxyquinoline-3-carboxamide

Produkt 1

HCID 1358226487,8-Dimethoxy-2-methyl-3H-pyrimido[4,5-b]quinolin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Concentrated sulfuric acid (1.5 ml.) is added to a slurry of 6,7-dimethoxy-2-aminoquinoline-3-carboxamide (5.0 g., 0.02 mole) and acetic anhydride (40 ml.). The slurry dissolves to give a dark orange solution from which a heavy yellow precipitate separates. Acetic anhydride (10 ml.) is added to facilitate stirring and heating continued for an additional 75 minutes. The mixture is cooled, water (50 ml.) added and the resulting solution made alkaline with 5N sodium hydroxide (225 ml.). It is chilled, the precipitate collected by filtration and air-dried. The yellow solid is recrystallized from ethanol. Yield = 2.37 g., M.P. 300°-302° (dec.).

Aufarbeitung

  1. dissolutionThe slurry dissolves
  2. customto give a dark orange solution from which a heavy yellow precipitate separates
  3. temperatureheating
  4. temperatureThe mixture is cooled
  5. temperatureIt is chilled
  6. filtrationthe precipitate collected by filtration
  7. customair-dried
  8. customThe yellow solid is recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-daed25dc30ac4bf4b6675c3ad778ef30
Quelldatensatz
uspto-grants-1978_10
Patentnummer
US04120962

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