Hydrochloric Acid → 6-[(Phenylsulfonyl)amino]quinoline-3-carboxylic acid

HRID 1894963Notes

Reaction equation

HRID 1894963 reaction equation
[C:1]1([S:7]([N:10](S(C2C=CC=CC=2)(=O)=O)[C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[N:17]=[CH:16][C:15]([C:21]([O:23]C)=[O:22])=[CH:14]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].O.Cl>CO.CN(C)C=O>[C:1]1([S:7]([NH:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[N:17]=[CH:16][C:15]([C:21]([OH:23])=[O:22])=[CH:14]3)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 67002239Methyl 6-[bis(phenylsulfonyl)amino]quinoline-3-carboxylate

Product 1

HCID 670023616-[(Phenylsulfonyl)amino]quinoline-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 6-[bis(phenylsulfonyl)amino]quinoline-3-carboxylate (0.29 g, 0.601 mmol) in methanol (2.4 mL) was added a 1 M solution of sodium hydroxide in H2O (2.4 mL, 2.4 mmol). N,N-dimethylformamide (1 mL) was added to aid solubility and the resulting suspension was stirred at room temperature for 48 h. The reaction was then warmed to 60° C. and stirred for 96 h. A solution of hydrochloric acid (1.0 M in water) was added until pH=7. The mixture was extracted with ethyl acetate three times. The extracts were combined, washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure and used as obtained (Int-12, 0.201 g, 61%). LC-MS: (FA) ES+ 329.

Workup

  1. temperatureThe reaction was then warmed to 60° C.
  2. stirringstirred for 96 h
  3. extractionThe mixture was extracted with ethyl acetate three times
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customas obtained (Int-12, 0.201 g, 61%)

Sources & evidence

ORD record
ord-c4dbde8d252b4dc185051571131428cf
Source dataset
uspto-grants-2013_08
Patent number
US08513421B2

Reaction notes

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