Hydrochloric Acid → HCID 22148747, compound

HRID 2422421Notes

Reaction equation

HRID 2422421 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 (45) (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 h. 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 47 (153 mg, 78%). 1H NMR (300 MHz, DMSO-d6) δ 7.16 (2H, s), 7.62 (1H, dd, J=2.0, 8.5 Hz), 7.73 (1H, d, J=2.9 Hz), 7.82 (1H, s), 8.08-8.11 (3H, m), 8.60 (1H, s), 8.95 (1H, d, J=2.9 Hz), 13.2 (1H, br s), MS (M+H) 557. mp 228-2.

Workup

  1. temperatureThis mixture was refluxed for 2.5 h
  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-1266bde9ae294771a65a3d3e55041a08
Source dataset
uspto-grants-2011_06
Patent number
US07960408B2

Reaction notes

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