4-Aminobenzoic Acid → 4-[[3-Ethoxycarbonyl-7-(trifluoromethyl)-4-quinolyl]amino]benzoic acid hydrochloride

HRID 648511

Reaction equation

HRID 648511 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17].[NH2:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=1>O1CCCC1>[ClH:1].[CH2:19]([O:18][C:16]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[NH:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=1)=[CH:10][CH:9]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:7]=2)=[O:17])[CH3:20]

Participants

4

Reactant 2

HCID 9784-Aminobenzoic AcidHCID 14515676Ethyl 4-chloro-7-(trifluoromethyl)quinoline-3-carboxylate

Product 1

HCID 138250354-[[3-Ethoxycarbonyl-7-(trifluoromethyl)-4-quinolyl]amino]benzoic acid hydrochlorideYield 61.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 4-chloro-7-(trifluoromethyl)-3-quinoline-carboxylate (3.04 g) and 4-aminobenzoic acid (1.37 g) in tetrahydrofuran (53 ml) was stirred under reflux for 10 hours and cooled to room temperature. The precipitates were collected and washed with tetrahydrofuran to give 4-[[3-ethoxycarbonyl-7-(trifluoromethyl)-4-quinolyl]amino]benzoic acid hydrochloride (2.69 g) as yellow powder.

Workup

  1. temperatureunder reflux for 10 hours
  2. customThe precipitates were collected
  3. washwashed with tetrahydrofuran

Sources & evidence

ORD record
ord-bebe478147bd4c42b33c1475c46188a7
Source dataset
uspto-grants-1988_04
Patent number
US04735952

Linked notes

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