Hydrochloric Acid → 4-phenyl-2-(4-(1H-pyrrol-1-yl)benzamido)benzoic acid

HRID 1673546Notes

Reaction equation

HRID 1673546 reaction equation
CO.[OH-].[Na+].[C:5]1([C:11]2[CH:23]=[CH:22][C:14]([C:15]([O:17]C(C)(C)C)=[O:16])=[C:13]([NH:24][C:25](=[O:37])[C:26]3[CH:31]=[CH:30][C:29]([N:32]4[CH:36]=[CH:35][CH:34]=[CH:33]4)=[CH:28][CH:27]=3)[CH:12]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl>C(OCC)(=O)C.O1CCOCC1>[C:5]1([C:11]2[CH:23]=[CH:22][C:14]([C:15]([OH:17])=[O:16])=[C:13]([NH:24][C:25](=[O:37])[C:26]3[CH:31]=[CH:30][C:29]([N:32]4[CH:33]=[CH:34][CH:35]=[CH:36]4)=[CH:28][CH:27]=3)[CH:12]=2)[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 67344178tert-butyl 4-phenyl-2-(4-(1H-pyrrol-1-yl)benzamido)benzoate

Product 1

HCID 578793464-phenyl-2-(4-(1H-pyrrol-1-yl)benzamido)benzoic acidYield 86%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

1.0 mL of methanol and 0.5 mL of 2.0 mol/L aqueous sodium hydroxide were added to 1.0 mL of dioxane solution containing 20 mg of tert-butyl 4-phenyl-2-(4-(1H-pyrrol-1-yl)benzamido)benzoate at room temperature and stirred at 50° C. for 30 minutes. Ethyl acetate and 1.0 mol/L hydrochloric acid were added after the reaction mixture was cooled to room temperature. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure, Diisopropyl ether were added to toe obtained residue and a solid substance was separated by filtration to obtain 15 mg of 4-phenyl-2-(4-(1H-pyrrol-1-yl)benzamido)benzoic acid as white solid.

Workup

  1. temperaturewas cooled to room temperature
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. washafter washed with a saturated sodium chloride aqueous solution
  5. customthe solvent was evaporated under reduced pressure, Diisopropyl ether
  6. additionwere added
  7. customto toe obtained residue
  8. customa solid substance was separated by filtration

Sources & evidence

ORD record
ord-42cbf5a0ad8f41e8942a4333a253c2b3
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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