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

HRID 34636Notes

Reaction equation

HRID 34636 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1C=CC=[C:10]1C=O.[F:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[C:32]3[C:27](=[CH:28][C:29]([F:39])=[C:30]([N:33]4[CH2:37][CH2:36][CH:35]([NH2:38])[CH2:34]4)[CH:31]=3)[C:26](=[O:40])[C:25]([C:41]([OH:43])=[O:42])=[CH:24]2)=[CH:19][CH:18]=1>>[F:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[C:32]3[C:27](=[CH:28][C:29]([F:39])=[C:30]([N:33]4[CH2:37][CH2:36][CH:35]([N:38]=[CH:1][C:2]5[CH:7]=[CH:6][C:5]([CH3:10])=[CH:4][CH:3]=5)[CH2:34]4)[CH:31]=3)[C:26](=[O:40])[C:25]([C:41]([OH:43])=[O:42])=[CH:24]2)=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 7362FurfuralHCID 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 2-furaldehyde and using the acid (1) (R=o,p-difluorophenyl) described in Example 7 one can obtain 1-o,p-difluorophenyl-6-fluoro-1,4-dihydro-4-oxo-7-(3-(2-furylidene)amino-1-pyrrolidinyl)-quinoline-3-carboxylic acid (3) (R=o,p-difluorophenyl, Z=2-furan).

Sources & evidence

ORD record
ord-1a191cc7e4e04639bdd01f241b0d1ede
Source dataset
uspto-grants-1988_08
Patent number
US04762845

Reaction notes

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