Acetic Acid → 6,7-Dimethoxy-4-(3-methoxy-2-methylanilino)-3-quinolinecarboxamide

HRID 1822851

Reaktionsgleichung

Reaktionsgleichung von HRID 1822851
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]([NH2:18])=[O:17].[CH3:19][O:20][C:21]1[C:22]([CH3:28])=[C:23]([CH:25]=[CH:26][CH:27]=1)[NH2:24].C(O)(=O)C.C([O-])(O)=O.[Na+]>CN(C=O)C.O>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][C:3]([C:16]([NH2:18])=[O:17])=[C:2]2[NH:24][C:23]1[CH:25]=[CH:26][CH:27]=[C:21]([O:20][CH3:19])[C:22]=1[CH3:28]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 118048223-Methoxy-2-methylanilineHCID 221702044-Chloro-6,7-dimethoxyquinoline-3-carboxamide

Produkt 1

HCID 221702436,7-Dimethoxy-4-(3-methoxy-2-methylanilino)-3-quinolinecarboxamideAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 4-chloro-6,7-dimethoxy-3-quinolinecarboxamide (0.046 g, 0.17 mmol), 3-methoxy-2-methylaniline (0.036 g, 0.26 mmol) and acetic acid (40 μl) in DMF (0.8 ml) was heated at 100° C. for 2.5 h. After cooling, the mixture was diluted with water (15 ml) and made alkaline with saturated NaHCO3. The resulting gummy precipitate was collected and crystallized from methanol-water to give the title compound (45 mg, 70%).

Aufarbeitung

  1. temperatureAfter cooling
  2. customThe resulting gummy precipitate was collected
  3. customcrystallized from methanol-water

Quellen und Nachweise

ORD-Eintrag
ord-cecbfc954e9c4795b263700ff40c03e4
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07037925B2

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