Lithium Hydroxide → 4-(Quinoline-8-sulfonamido)benzoic acid

HRID 1626327

Reaction equation

HRID 1626327 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[S:11]([NH:14][C:15]2[CH:25]=[CH:24][C:18]([C:19]([O:21]CC)=[O:20])=[CH:17][CH:16]=2)(=[O:13])=[O:12])[CH:4]=[CH:3][CH:2]=1.[Li+].[OH-]>C1COCC1.O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[S:11]([NH:14][C:15]2[CH:25]=[CH:24][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=2)(=[O:13])=[O:12])[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 1357549Ethyl 4-(quinoline-8-sulfonamido)benzoate

Product 1

HCID 7766454-(Quinoline-8-sulfonamido)benzoic acid

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a stirred solution of ethyl 4-(quinoline-8-sulfonamido)benzoate 90 (8 gm, 22.4 mmol) in THF:H2O (1:1) under nitrogen atmosphere was added solid LiOH (9.4 gm, 224 mmol) at RT. The solution was then refluxed for 6 hr. After completion of the reaction, the reaction mixture was washed with ethyl acetate (2×100 ml) to remove non polar impurities. The aqueous layer was acidified (pH 4) with citric acid solution. The resultant precipitate was filtered out and air-dried. The traces of water were removed by co-distillation with toluene. The resultant off white solid (5.9 gm, 80%) was taken to the next step without further purification.

Workup

  1. temperatureThe solution was then refluxed for 6 hr
  2. customAfter completion of the reaction
  3. washthe reaction mixture was washed with ethyl acetate (2×100 ml)
  4. customto remove non polar impurities
  5. filtrationThe resultant precipitate was filtered out and
  6. customair-dried
  7. customThe traces of water were removed by co-distillation with toluene
  8. customThe resultant off white solid (5.9 gm, 80%) was taken to the next step without further purification

Sources & evidence

ORD record
ord-adaaed4630d94ce88c0c71d6866a79cf
Source dataset
uspto-grants-2014_07
Patent number
US08785450B2

Linked notes

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