4-Aminobenzoic Acid → 4-(Quinoline-8-sulfonamido)benzoic acid

HRID 514799

Reaction equation

HRID 514799 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.N1C=CC=CC=1.[N:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][C:25]=2[S:27](Cl)(=[O:29])=[O:28])[CH:20]=[CH:19][CH:18]=1>C1COCC1>[N:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][C:25]=2[S:27]([NH:1][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=2)(=[O:29])=[O:28])[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 9784-Aminobenzoic AcidHCID 1049PyridineHCID 292208-Quinolinesulfonyl chloride

Product 1

HCID 7766454-(Quinoline-8-sulfonamido)benzoic acidYield 58.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-aminobenzoic acid (10 g, 73 mmol) in 100 mL of anhydrous THF was added pyridine (1.15 g, 146 mmol), and quinoline-8-sulfonyl chloride (20 g, 88 mmol) at 0° C. The resulting mixture was stirred at 70° C. overnight. After filtration, the residue was washed with EtOH and 14 g of title compound was obtained as pure product.

Workup

  1. filtrationAfter filtration
  2. washthe residue was washed with EtOH

Sources & evidence

ORD record
ord-ede0bf0528ba4e8186dfcc4f9fff99be
Source dataset
uspto-grants-2015_08
Patent number
US09108921B2

Linked notes

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