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

HRID 34645Notes

Reaction equation

HRID 34645 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][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]([O:9][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 1264-HydroxybenzaldehydeHCID 240BenzaldehydeHCID 135006571-p-Fluorophenyl-6-fluoro-1,4-dihydro-4-oxo-7-(3-amino-1-pyrrolidinyl)-quinoline-3-carboxylic acid

Product 1

HCID 142300191-p-Fluorophenyl-6-fluoro-1,4-dihydro-4-oxo-7-(3-(4-methoxybenzylidene)amino-1-pyrrolidinyl)-quinoline-3-carboxylic acid

Procedure

In the described fashion of Example 1 replacing benzaldehyde with 4-hydroxybenzaldehyde and using the acid (1) (R=cyclopropyl) described in Example 19 one obtains 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(3-(4-hydroxybenzylidene)amino-1-pyrrolidinyl)-quinoline-3-carboxylic acid (3) (R=cyclopropyl, Z=p-hydroxyphenyl); m.p. 273°-275° C.; Mass Spectrum, M/Z 435. Analytical Calculation for C24H22FN3O4.1/2H2O: C, 66.21; H, 5.06; N, 9.65. Found: C, 64.83; H, 5.01; N, 9.13.

Sources & evidence

ORD record
ord-54f00010d73a4fe7ad0b47e6da20449b
Source dataset
uspto-grants-1988_08
Patent number
US04762845

Reaction notes

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