N-[(4-chlorophenyl)methyl]-6-(3-hydroxyprop-1-ynyl)-1-methyl-4-oxo-quinoline-3-carboxamide → N-(4-Chlorobenzyl)-6-(3-hydroxypropyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide

HRID 1067983Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1067983
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:21]#[C:22][CH2:23][OH:24])[CH:17]=3)[N:12]([CH3:25])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.[H][H]>[Pt].C1COCC1.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:21][CH2:22][CH2:23][OH:24])[CH:17]=3)[N:12]([CH3:25])[CH:11]=2)=[O:9])=[CH:26][CH:27]=1

Komponenten

5

Edukt 2

HCID 11740538N-[(4-chlorophenyl)methyl]-6-(3-hydroxyprop-1-ynyl)-1-methyl-4-oxo-quinoline-3-carboxamideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 9800255N-(4-Chlorobenzyl)-6-(3-hydroxypropyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamideAusbeute 89,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23939PlatinumKatalysatorHCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 0.50 g of N-(4-chlorobenzyl)-6-(3-hydroxy-1-propynyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide from Example No. 31 and 50 mg of 5% platinum on carbon catalyst in 20 mL of 1:1 THF-methanol is stirred under 1 atm hydrogen for 3 h, then filtered through diatomaceous earth. The filtrate is concentrated under reduced pressure and the residual solid flash chromatographed on silica gel using 4-5% methanol in dichloromethane to afford 0.45 g of the title compound as a yellow solid. Further purification is achieved by recrystallization of the solid from 15 mL of acetonitrile.

Aufarbeitung

  1. filtrationfiltered through diatomaceous earth
  2. concentrationThe filtrate is concentrated under reduced pressure
  3. customthe residual solid flash chromatographed on silica gel using 4-5% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-fe153a5ea78d4b94882bbb0fabddbf55
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06248739B1

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