Sodium Azide → 3-Azidomethyl-7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester

HRID 1887817

Reaktionsgleichung

Reaktionsgleichung von HRID 1887817
Br[CH2:2][C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][C:8]([Cl:14])=[CH:9][CH:10]=2)[N:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:4]=1[C:21]([O:23][CH3:24])=[O:22].[N-:25]=[N+:26]=[N-:27].[Na+]>CN(C=O)C>[CH3:24][O:23][C:21]([C:4]1[N:5]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:6]2[C:11]([C:12](=[O:13])[C:3]=1[CH2:2][N:25]=[N+:26]=[N-:27])=[CH:10][CH:9]=[C:8]([Cl:14])[CH:7]=2)=[O:22]

Komponenten

4

Edukt 2

HCID 33557Sodium AzideHCID 86672058Methyl 3-(bromomethyl)-7-chloro-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxylate

Produkt 1

HCID 712088133-Azidomethyl-7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl esterAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In a 250 mL round-bottomed flask, methyl 3-(bromomethyl)-7-chloro-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxylate (2.7 g, 6.64 mmol) and sodium azide (1.25 g, 19.2 mmol) were combined with DMF (40 mL). The reaction mixture was stirred at room temperature overnight, then it was concentrated and triturated in ethyl acetate. The product 3-azidomethyl-7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester (2.3 g, 94%) was obtained as a white solid.

Aufarbeitung

  1. concentrationit was concentrated
  2. customtriturated in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-acf3a7293e4e4c8b9bc2d26b46ada740
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501732B2

Verknüpfte Notizen

Wird geladen…