Chlorosuccinimide → 3-Chloromethylthio-7-fluoro-1-methyl-4-quinolone

HRID 1823812

Reaktionsgleichung

Reaktionsgleichung von HRID 1823812
[CH3:1][N:2]1[C:8]2[CH:9]=[C:10]([F:13])[CH:11]=[CH:12][C:7]=2[C:5](=[O:6])[C:4]([S+:14]([O-])[CH3:15])=[CH:3]1.FC1C=C2C(C(=S)C(C)=CN2C)=CC=1.[Cl:31]N1C(=O)CCC1=O>>[Cl:31][CH2:15][S:14][C:4]1[C:5](=[O:6])[C:7]2[C:8](=[CH:9][C:10]([F:13])=[CH:11][CH:12]=2)[N:2]([CH3:1])[CH:3]=1

Komponenten

4

Edukt 3

HCID 31398ChlorosuccinimideHCID 865891517-Fluoro-1-methyl-3-methylthio-4-quinoloneHCID 178481179HCID 178481179, Verbindung

Produkt 1

HCID 104452083-Chloromethylthio-7-fluoro-1-methyl-4-quinolone

Versuchsvorschrift

In other embodiments, the synthesis of racemic monochloroflosequinan is carried out as a three step procedure, as described in more detail in Example 2. Briefly, in the first step, racemic flosequinan is reduced to desoxyflosequinan (7-fluoro-1-methyl-3-methylthio-4-quinolone). In the second step, desoxyflosequinan is chlorinated using N-chlorosuccinimide, to produce chlorodesoxyflosequinan (3-chloromethylthio-7-fluoro-1-methyl-4-quinolone). In the third step, chlorodesoxyflosequinan is subjected to oxidation to produce 3-chloromethylsulfinyl-7-fluoro-1-methyl-4-quinolone (monochloroflosequinan). Such oxidation may be accomplished using hydrogen peroxide.

Aufarbeitung

  1. customIn other embodiments, the synthesis of racemic monochloroflosequinan

Quellen und Nachweise

ORD-Eintrag
ord-111e4bb3897742598ea1fd5eb9eaa3a6
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07041677B2

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