4-Aminobenzoic Acid → 4-[(4-Carboxyphenyl)amino]-7-chloro-3-quinolinecarboxylic acid ethyl ester hydrochloride

HRID 1755941Notes

Reaction equation

HRID 1755941 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:16])=[CH:13][CH:12]=[C:11]([Cl:17])[CH:10]=2)=[O:5])[CH3:2].[NH2:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1>C1COCC1>[ClH:16].[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1)=[CH:13][CH:12]=[C:11]([Cl:17])[CH:10]=2)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 9784-Aminobenzoic AcidHCID 12256460Ethyl 4,7-dichloroquinoline-3-carboxylate

Product 1

HCID 677832854-[(4-Carboxyphenyl)amino]-7-chloro-3-quinolinecarboxylic acid ethyl ester hydrochlorideYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4,7-Dichloro-3-quinolinecarboxylic acid ethyl ester (72.0 g, 267 mmol) and p-aminobenzoic acid (36.6 g, 267 mmol) were refluxed in 675 ml of THF for 6 h then cooled to room temperature. The yellow precipitate was filtered, combined with the product from a 10 mmol reaction and washed with THF, then ether. The yellow powder was then dried in vacuo overnight affording 82.7 g (203 mmol, 73% yield) of 4-[(4-carboxyphenyl)amino]-7-chloro-3-quinolinecarboxylic acid ethyl ester hydrochloride.

Workup

  1. filtrationThe yellow precipitate was filtered
  2. customcombined with the product from a 10 mmol reaction
  3. washwashed with THF
  4. customThe yellow powder was then dried in vacuo overnight

Sources & evidence

ORD record
ord-0890b71408db4f55b4d37cdc0a133008
Source dataset
uspto-grants-1995_08
Patent number
US05438064

Reaction notes

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