Hydrochloric Acid → HCID 22148747, compound

HRID 1835515Notes

Reaction equation

HRID 1835515 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][C:9]([O:15][C:16]1[C:21]([Cl:22])=[CH:20][C:19]([NH:23][S:24]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=3[Cl:34])(=[O:26])=[O:25])=[CH:18][C:17]=1[Cl:35])=[CH:8]2)=[O:4].[OH-].[Na+].Cl>C1COCC1.CO>[Cl:22][C:21]1[CH:20]=[C:19]([NH:23][S:24]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=2[Cl:34])(=[O:26])=[O:25])[CH:18]=[C:17]([Cl:35])[C:16]=1[O:15][C:9]1[CH:10]=[N:11][C:12]2[C:7]([CH:8]=1)=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:14][CH:13]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67243569HCID 67243569, compound

Product 1

HCID 22148747HCID 22148747, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 3-[2,6-Dichloro-4-(2,4-dichloro-benzenesulfonylamino)-phenoxy]-quinoline-6-carboxylic acid methyl ester (181) (200 mg, 0.35 mmol) in THF/MeOH(2 ml/2 ml) was added 4N NaOH (0.1 ml, 0.4 mmol). This mixture was refluxed for 2.5 hr. The reaction mixture was cooled to room temperature and was neutralized with 2N HCl, and then concentrated. The residue was extracted twice with AcOEt. Organic layer was washed by Brine, dried over anhydrous MgSO4, and concentrated to give a solid. Crude product was recrystallized by Hexane/AcOEt to afford compound 183 (153 mg, 78%).

Workup

  1. temperatureThis mixture was refluxed for 2.5 hr
  2. concentrationconcentrated
  3. extractionThe residue was extracted twice with AcOEt
  4. washOrganic layer was washed by Brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated
  7. customto give a solid
  8. customCrude product was recrystallized by Hexane/AcOEt

Sources & evidence

ORD record
ord-33b7cb6230194403a41110c8aabe55f4
Source dataset
uspto-grants-2004_08
Patent number
US06770648B2

Reaction notes

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