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

HRID 1626325Notes

Reaction equation

HRID 1626325 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 acidYield 90%

Reagents, catalysts & solvents 1

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

Procedure

Ethyl 4-(quinoline-8-sulfonamido)benzoate (90, 10 g, 28.08 mmol) was dissolved in a mixture of THF-water (100:100 ml) and maintained at room temperature. To this solution was added LiOH (5.89 g, 14.0 mmol) and the resultant solution was refluxed overnight. The reaction mixture was then washed with ethyl acetate (3×50 ml) and then acidified with dilute HCl. The resultant suspension was filtered and residue was co-distilled with toluene. This product was then dried under vacuum to yield carboxylic acid 91 (8.28 g, 90%) as an off-white solid.

Workup

  1. washThe reaction mixture was then washed with ethyl acetate (3×50 ml)
  2. filtrationThe resultant suspension was filtered
  3. customThis product was then dried under vacuum

Sources & evidence

ORD record
ord-f6d1d7d630fc4805bec109b7845bd3c3
Source dataset
uspto-grants-2014_07
Patent number
US08785450B2

Reaction notes

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