3-Nitrobenzaldehyde → Clinafloxacin hydrochloride, (S)-

HRID 265696Notes

Reaction equation

HRID 265696 reaction equation
[N+](C1C=C(C=CC=1)C=O)([O-])=O.[NH2:12][C@H:13]1[CH2:17][CH2:16][NH:15][CH2:14]1.[Cl:18][C:19]1[C:20](F)=[C:21]([F:36])[CH:22]=[C:23]2[C:28]=1[N:27]([CH:29]1[CH2:31][CH2:30]1)[CH:26]=[C:25]([C:32]([OH:34])=[O:33])[C:24]2=[O:35]>>[ClH:18].[NH2:12][C@H:13]1[CH2:17][CH2:16][N:15]([C:20]2[C:19]([Cl:18])=[C:28]3[C:23]([C:24](=[O:35])[C:25]([C:32]([OH:34])=[O:33])=[CH:26][N:27]3[CH:29]3[CH2:31][CH2:30]3)=[CH:22][C:21]=2[F:36])[CH2:14]1

Participants

4

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 1519351(3S)-(-)-3-AminopyrrolidineHCID 98359418-Chloro-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 66618483Clinafloxacin hydrochloride, (S)-

Procedure

If, for example, the reaction mixture of 3-nitrobenzaldehyde and (S)-3-aminopyrrolidine 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-qninolinecarboxylic 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##

Workup

  1. customthe 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-qninolinecarboxylic acid

Sources & evidence

ORD record
ord-6442d14549844345b83b32a23efadd9e
Source dataset
uspto-grants-1997_07
Patent number
US05648493

Reaction notes

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