2-Chloroquinoline-3-carboxylic acid → 6-Bromo-2-{1-carboxy-2-[4-(3-carboxy-quinolin-2-yloxy)-phenyl]-ethylamino}-quinoline-3-carboxylic acid

HRID 2065672Notes

Reaction equation

HRID 2065672 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:12][CH:13]([C:22]([OH:24])=[O:23])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)[C:6]([C:25]([OH:27])=[O:26])=[CH:5]2.Cl[C:29]1[C:38]([C:39]([OH:41])=[O:40])=[CH:37][C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[N:30]=1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:12][CH:13]([C:22]([OH:24])=[O:23])[CH2:14][C:15]1[CH:16]=[CH:17][C:18]([O:21][C:29]3[C:38]([C:39]([OH:41])=[O:40])=[CH:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=3)=[CH:19][CH:20]=1)[C:6]([C:25]([OH:27])=[O:26])=[CH:5]2

Participants

3

Reactant 2

HCID 8471632-Chloroquinoline-3-carboxylic acidHCID 452565296-Bromo-2-[1-carboxy-2-(4-hydroxy-phenyl)-ethylamino]-quinoline-3-carboxylic acid

Product 1

HCID 452565306-Bromo-2-{1-carboxy-2-[4-(3-carboxy-quinolin-2-yloxy)-phenyl]-ethylamino}-quinoline-3-carboxylic acid

Procedure

In close analogy to the procedure described in Example 96, 6-bromo-2-[1-carboxy-2-(4-hydroxy-phenyl)-ethylamino]-quinoline-3-carboxylic acid is reacted with 2-chloro-quinoline-3-carboxylic acid to provide the title compound in good yield.

Sources & evidence

ORD record
ord-30a5ea7e1b7541999c0b410db3c7ae70
Source dataset
uspto-grants-2012_10
Patent number
US08288549B2

Reaction notes

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