Methyl iodide → N-(4-Chlorobenzyl)-6-(hydroxymethyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide

HRID 1067944

Reaktionsgleichung

Reaktionsgleichung von HRID 1067944
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([CH2:21][OH:22])=[CH:15][CH:14]=3)=[O:9])=[CH:4][CH:3]=1.[C:25]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C.O>[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][OH:22])[CH:17]=3)[N:12]([CH3:25])[CH:11]=2)=[O:9])=[CH:23][CH:24]=1

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178522872HCID 178522872, Verbindung

Produkt 1

HCID 15516933N-(4-Chlorobenzyl)-6-(hydroxymethyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamideAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of N-(4-chlorobenzyl)-4-hydroxy-6-(hydroxymethyl)-3-quinolinecarboxamide from Preparation No. 9 (300 mg,), K2CO3 (485.1 mg), and CH3I (0.11 mL) in 4 mL anhydrous DMF is heated at 90° C. for 3 h. The reaction is cooled to room temperature and diluted with H2O to dissolve any salts and precipitate the product. The crude product is adsorbed onto silica and chromatographed eluting with 3% MeOH in CH2Cl2. Fractions homogenous by TLC are combined and condensed to afford 154.2 mg (49%) of the title compound as a white solid.

Aufarbeitung

  1. dissolutionto dissolve any salts
  2. customprecipitate the product
  3. customchromatographed
  4. washeluting with 3% MeOH in CH2Cl2
  5. customcondensed

Quellen und Nachweise

ORD-Eintrag
ord-7fa2b8efe89340fbb34b36f934679723
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06248739B1

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