Dimethylformamide → 6-amino-N-[(4-chlorophenyl)methyl]-4-hydroxy-3-quinolinecarboxamide

HRID 2289915Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2289915
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][C:18]([N+:23]([O-])=O)=[CH:17][CH:16]=3)=[O:11])=[CH:4][CH:3]=1.CN(C)C=O.[H][H]>[Ni].O>[NH2:23][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][C:12]([C:10]([NH:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:11])=[C:21]2[OH:22]

Komponenten

6

Edukt 3

HCID 6228DimethylformamideHCID 178418361HCID 178418361, VerbindungHCID 178522883HCID 178522883, Verbindung

Produkt 1

HCID 1785073346-amino-N-[(4-chlorophenyl)methyl]-4-hydroxy-3-quinolinecarboxamideAusbeute 84,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

N-[(4-chlorophenyl)methyl]-4-hydroxy-6-nitro-3-quinolinecarboxamide (500 mg) is suspended in 50 mL of freshly degassed dimethylformamide and treated with 0.5 mL of 50% Raney nickel in water (Aldrich). The mixture is agitated under 45 psi hydrogen pressure for 24 h, and then it is filtered through celite. The solvent is removed by evaporation at reduced pressure and the residue is suspended in 5 mL of absolute ethanol and it is collected by filtration. After drying at 0.1 torr/100 ° C./1.5 h, the product is obtained as 387 mg of a pale yellow powder.

Aufarbeitung

  1. filtrationit is filtered through celite
  2. customThe solvent is removed by evaporation at reduced pressure
  3. filtrationit is collected by filtration
  4. customAfter drying at 0.1 torr/100 ° C./1.5 h

Quellen und Nachweise

ORD-Eintrag
ord-29cca363d5bb404f9c8c50532aac403f
Quelldatensatz
uspto-grants-2000_07
Patentnummer
US06093732

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