3-Nitrobenzaldehyde → Clinafloxacin hydrochloride, (S)-

HRID 346315

Reaktionsgleichung

Reaktionsgleichung von HRID 346315
[N+](C1C=C(C=CC=1)C=O)([O-])=O.[Cl:12]C1C(F)=C(F)C=C2C=1N(C1CC1)C=C(C(O)=O)C2=O.[Cl:32][C:33]1[C:34]([N:51]2[CH2:55][CH2:54][C@H:53]([N:56]=CC3C=CC=C([N+]([O-])=O)C=3)[CH2:52]2)=[C:35]([F:50])[CH:36]=[C:37]2[C:42]=1[N:41]([CH:43]1[CH2:45][CH2:44]1)[CH:40]=[C:39]([C:46]([OH:48])=[O:47])[C:38]2=[O:49]>>[ClH:12].[NH2:56][C@H:53]1[CH2:54][CH2:55][N:51]([C:34]2[C:33]([Cl:32])=[C:42]3[C:37]([C:38](=[O:49])[C:39]([C:46]([OH:48])=[O:47])=[CH:40][N:41]3[CH:43]3[CH2:44][CH2:45]3)=[CH:36][C:35]=2[F:50])[CH2:52]1

Komponenten

4

Edukt 3

HCID 74493-NitrobenzaldehydeHCID 98359418-Chloro-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 541172038-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-7-[(S)-3-(3-nitrobenzylideneamino)-1-pyrrolidinyl]-4-oxo-3-quinolinecarboxylic acid

Produkt 1

HCID 66618483Clinafloxacin hydrochloride, (S)-

Versuchsvorschrift

If, for example, the reaction mixture of 3-nitrobenzaldehyde and (S)-3-aminopyrrolidne is reacted with 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid in a one-pot reaction, the course of the reaction via the intermediately formed 8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-7-[(S)-3-(3-nitrobenzylideneamino)-1-pyrrolidinyl]-4-oxo-3-quinolinecarboxylic acid to give 7-[(S)-3-amino-1-pyrrolidinyl]-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid hydrochloride can be represented by the following equation: ##STR22##

Quellen und Nachweise

ORD-Eintrag
ord-a565a44b42cf4f2b8505b216a4f0b3ca
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05061712

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