Hydrochloric Acid → HCID 57879447, compound

HRID 1673512Notes

Reaction equation

HRID 1673512 reaction equation
[OH-].[Na+].O1CCOCC1.[C:9]([NH:17][C:18]1[CH:30]=[C:29]([N:31]2[CH:35]=[CH:34][CH:33]=[CH:32]2)[CH:28]=[CH:27][C:19]=1[C:20]([O:22]C(C)(C)C)=[O:21])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl>C(OCC)(=O)C.O.CO>[C:9]([NH:17][C:18]1[CH:30]=[C:29]([N:31]2[CH:35]=[CH:34][CH:33]=[CH:32]2)[CH:28]=[CH:27][C:19]=1[C:20]([OH:22])=[O:21])(=[O:16])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 67343296HCID 67343296, compound

Product 1

HCID 57879447HCID 57879447, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

0.24 mL of 2.0 mol/L aqueous sodium hydroxide was added to a mixed solution of 1.0 mL of dioxane and 1.0 mL of methanol containing 58 mg of tert-butyl 2-(benzamido)-4-(1H-pyrrol-1-yl)benzoate and stirred at 50° C. for 1 hour and 30 minutes. After the reaction mixture was cooled to room temperature, water was added and after pH was adjusted to pH 3.0 with 1.0 mol/L hydrochloric acid, ethyl acetate was added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with water and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. Diisopropyl ether were added to the obtained residue and a solid substance was separated by filtration to obtain 41 mg of 2-(benzamido)-4-(1H-pyrrol-1-yl)benzoic acid as white solid.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. additionwas added
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. washafter washed with water
  6. customa saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure
  7. additionDiisopropyl ether were added to the obtained residue
  8. customa solid substance was separated by filtration

Sources & evidence

ORD record
ord-d0f375949f244664b89b4019403e7051
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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