Benzaldehyde → 1-p-Fluorophenyl-6-fluoro-1,4-dihydro-4-oxo-7-(3-(4-methylbenzylidene)amino-1-pyrrolidinyl)-quinoline-3-carboxylic acid

HRID 34641Notes

Reaction equation

HRID 34641 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[C:10]1C=CC(C=O)=CC=1.[F:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[C:34]3[C:29](=[CH:30][C:31]([F:41])=[C:32]([N:35]4[CH2:39][CH2:38][CH:37]([NH2:40])[CH2:36]4)[CH:33]=3)[C:28](=[O:42])[C:27]([C:43]([OH:45])=[O:44])=[CH:26]2)=[CH:21][CH:20]=1>>[F:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[C:34]3[C:29](=[CH:30][C:31]([F:41])=[C:32]([N:35]4[CH2:39][CH2:38][CH:37]([N:40]=[CH:1][C:2]5[CH:7]=[CH:6][C:5]([CH3:10])=[CH:4][CH:3]=5)[CH2:36]4)[CH:33]=3)[C:28](=[O:42])[C:27]([C:43]([OH:45])=[O:44])=[CH:26]2)=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 680234-FluorobenzaldehydeHCID 135006571-p-Fluorophenyl-6-fluoro-1,4-dihydro-4-oxo-7-(3-amino-1-pyrrolidinyl)-quinoline-3-carboxylic acid

Product 1

HCID 142300121-p-Fluorophenyl-6-fluoro-1,4-dihydro-4-oxo-7-(3-(4-methylbenzylidene)amino-1-pyrrolidinyl)-quinoline-3-carboxylic acid

Procedure

In the described fashion of Example 1 replacing benzaldehyde and p-fluorobenzaldehyde and using the acid (1) (R=cyclopropyl) described in Example 19 one obtains 1 cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(3-(p-fluorobenzylidene)amino-1-pyrrolidinyl)-quinoline-3-carboxylic acid (3) (R=cyclopropyl, Z=p-fluorophenyl). mp 228°-229° C.

Sources & evidence

ORD record
ord-ee20f050eb1d4574be5d0bef495c23e6
Source dataset
uspto-grants-1988_08
Patent number
US04762845

Reaction notes

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