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

HRID 34638Notes

Reaction equation

HRID 34638 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC(C=O)=C[CH:10]=1.[F:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:33]3[C:28](=[CH:29][C:30]([F:40])=[C:31]([N:34]4[CH2:38][CH2:37][CH:36]([NH2:39])[CH2:35]4)[CH:32]=3)[C:27](=[O:41])[C:26]([C:42]([OH:44])=[O:43])=[CH:25]2)=[CH:20][CH:19]=1>>[F:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:33]3[C:28](=[CH:29][C:30]([F:40])=[C:31]([N:34]4[CH2:38][CH2:37][CH:36]([N:39]=[CH:1][C:2]5[CH:7]=[CH:6][C:5]([CH3:10])=[CH:4][CH:3]=5)[CH2:35]4)[CH:32]=3)[C:27](=[O:41])[C:26]([C:42]([OH:44])=[O:43])=[CH:25]2)=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 133894-PyridinecarboxaldehydeHCID 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 with 4-pyridinecarboxaldehyde and using the acid (1) (R=ethyl) described in Example 13 one obtains 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(3-(4-pyridylidene)amino-1-pyrrolidinyl)-quinoline-3-carboxylic acid (3) (R=ethyl, Z=4-pyridine).

Sources & evidence

ORD record
ord-23a0956c7bd448da90d48f287b21c7ef
Source dataset
uspto-grants-1988_08
Patent number
US04762845

Reaction notes

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