8-Quinolinesulfonyl chloride → 5-Fluoro-2-[(quinoline-8-sulfonyl)amino]benzoic acid

HRID 425102Notes

Reaction equation

HRID 425102 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].C(=O)([O-])O.[Na+].[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>O.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:11][S:27]([C:25]2[CH:24]=[CH:23][CH:22]=[C:21]3[C:26]=2[N:17]=[CH:18][CH:19]=[CH:20]3)(=[O:28])=[O:29])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

6

Reactant 3

HCID 292208-Quinolinesulfonyl chlorideHCID 1014122-Amino-5-fluorobenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 223986725-Fluoro-2-[(quinoline-8-sulfonyl)amino]benzoic acidYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A reaction mixture of 10.0 g (64 mmol) of 5-fluoro-2-aminobenzoic acid, 16.3 g (193 mmol) of sodium hydrogencarbonate and 16.3 g of 8-quinoline-sulfonyl chloride in 325 ml of water and 325 ml of ethyl acetate was stirred overnight at RT. The aqueous phase was separated off and extracted once with 50 ml of ethyl acetate. The aqueous phase was then rendered acidic using conc. hydrochloric acid and stirred for 2 h. The precipitate deposited was filtered off with suction, dried in vacuo and 19.5 g of 5-fluoro-2-(quinoline-8-sulfonylamino)benzoic acid were obtained.

Workup

  1. customThe aqueous phase was separated off
  2. extractionextracted once with 50 ml of ethyl acetate
  3. stirringstirred for 2 h
  4. filtrationThe precipitate deposited was filtered off with suction
  5. customdried in vacuo

Sources & evidence

ORD record
ord-8571394e9527468eb515e41bc4a2429f
Source dataset
uspto-grants-2012_01
Patent number
US08106099B2

Reaction notes

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