Hydrochloric Acid → 7-Chloro-4-hydroxy-2-(3,4-dimethoxyphenyl)-1,2,5,10-tetrahydropyridazino[4,5-b]quinoline-1,10-dione

HRID 1600051

Reaktionsgleichung

Reaktionsgleichung von HRID 1600051
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:19])[C:7]([C:15]([O:17]C)=O)=[C:8]([C:12](Cl)=[O:13])[NH:9]2)=[CH:4][CH:3]=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([NH:30][NH2:31])[CH:25]=[CH:26][C:27]=1[O:28][CH3:29].Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:19])[C:7]3[C:15](=[O:17])[N:30]([C:24]4[CH:25]=[CH:26][C:27]([O:28][CH3:29])=[C:22]([O:21][CH3:20])[CH:23]=4)[N:31]=[C:12]([OH:13])[C:8]=3[NH:9][C:10]=2[CH:11]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 88491(3,4-Dimethoxyphenyl)hydrazineHCID 219976803-Carbomethoxy-7-chloro-4-hydroxyquinoline-2-carbonyl chloride

Produkt 1

HCID 1784920847-Chloro-4-hydroxy-2-(3,4-dimethoxyphenyl)-1,2,5,10-tetrahydropyridazino[4,5-b]quinoline-1,10-dioneAusbeute 10,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

7-Chloro-3-methoxycarbonyl-4-oxo-1,4-dihydroquinoline-2-carbonyl chloride (7.00 g, 23.3 mM) was dissolved in tetrahydrofuran (210 mL) and added dropwise over 20 minutes to a cold (0° C.) solution of 3,4-dimethoxyphenylhydrazine (9.80 g, 58.3 mM) in tetrahydrofuran (420 mL)with stirring. The resulting brown suspension was stirred at 0° C. for 30 minutes and at room temperature for 2 hours. Ice/water slurry (450 mL) was added to the reaction mixture followed by 1N HCl (1.2 L) and the brown suspension was stirred for 1 hour. The solids were separated by filtration and washed with water and then ether to provide7-chloro-3-methoxycarbonyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acid N-2-(2,4-dimethoxyphenyl)hydrazide (15 g, wet). The combined filtrateand washes were partially concentrated to remove the THF whereupon a precipitate formed. This precipitate was collected and washed with water and then ether to give the crude title compound (2.00 g). Recrystallization of this crude from refluxing methanol (500 mL) gave the title compound (0.98 g, 10%) as a tan powder, mp=334°-336° C.; HS(CI): 400 (M+H).

Aufarbeitung

  1. stirringThe resulting brown suspension was stirred at 0° C. for 30 minutes and at room temperature for 2 hours
  2. stirringthe brown suspension was stirred for 1 hour
  3. customThe solids were separated by filtration
  4. washwashed with water
  5. concentrationThe combined filtrateand washes were partially concentrated
  6. customto remove the THF whereupon a precipitate
  7. customformed
  8. customThis precipitate was collected
  9. washwashed with water
  10. customether to give the crude title compound (2.00 g)
  11. customRecrystallization of this crude
  12. temperaturefrom refluxing methanol (500 mL)

Quellen und Nachweise

ORD-Eintrag
ord-657dea9b8ce742fca0fe7e5df0830b13
Quelldatensatz
uspto-grants-1998_04
Patentnummer
US05744471

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