Acetic Acid → 4-(3-Hydroxy-2-methylanilino)-6,7-dimethoxy-3-quinolinecarboxamide

HRID 1822850

Reaktionsgleichung

Reaktionsgleichung von HRID 1822850
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].[NH2:19][C:20]1[C:21]([CH3:27])=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=1.C(O)(=O)C.C([O-])(O)=O.[Na+]>CN(C=O)C.O>[OH:26][C:22]1[C:21]([CH3:27])=[C:20]([CH:25]=[CH:24][CH:23]=1)[NH:19][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]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 1044482-Amino-o-cresolHCID 516892Sodium BicarbonateHCID 221702044-Chloro-6,7-dimethoxyquinoline-3-carboxamide

Produkt 1

HCID 221702874-(3-Hydroxy-2-methylanilino)-6,7-dimethoxy-3-quinolinecarboxamide

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-amino-2-methylphenol (0.032 g, 0.26 mmol) and acetic acid (40 μl) in DMF (0.8 ml) was heated at 100° C. for 1.5 h. After cooling, the mixture was diluted with water (15 ml) and made alkaline with saturated NaHCO3. The title compound, which slowly precipitated was filtered off and dried to give 34 mg (55%).

Aufarbeitung

  1. temperatureAfter cooling
  2. customThe title compound, which slowly precipitated
  3. filtrationwas filtered off
  4. customdried
  5. customto give 34 mg (55%)

Quellen und Nachweise

ORD-Eintrag
ord-6ac3fe1c14f142949459a367b77b9200
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07037925B2

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