Hydrochloric Acid → HCID 57879382, compound

HRID 1673554Notes

Reaction equation

HRID 1673554 reaction equation
[OH-].[Na+].O1CCOCC1.[C:9]([NH:17][C:18]1[CH:27]=[C:26]([O:28][C:29]2[CH:30]=[C:31]3[C:35](=[CH:36][CH:37]=2)[N:34]([CH3:38])[CH:33]=[CH:32]3)[CH:25]=[CH:24][C:19]=1[C:20]([O:22]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:27]=[C:26]([O:28][C:29]2[CH:30]=[C:31]3[C:35](=[CH:36][CH:37]=2)[N:34]([CH3:38])[CH:33]=[CH:32]3)[CH:25]=[CH:24][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 Hydroxide2×HCID 312751,4-DioxaneHCID 57879499HCID 57879499, compound

Product 1

HCID 57879382HCID 57879382, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

0.094 mL of 2.0 mol/L aqueous sodium hydroxide was added to a mixed solution of 1.5 mL of dioxane and 1.5 mL of methanol containing 50 mg of methyl 2-(benzamido)-4-(1-methyl-1H-indol-5-yloxy)benzoate at room temperature, stirred at 50° C. for 1 hour, and 0.031 mL of 2.0 mol/L aqueous sodium hydroxide was added at the same temperature and then stirred at 50° C. for 30 minutes. After the reaction mixture was cooled to room temperature, water was added and pH was adjusted to pH 3.5 with 1.0 mol/L hydrochloric acid and 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. Hexane was added to the obtained residue and a solid substance was separated by filtration to obtain 37 mg of 2-(benzamido)-4-(1-methyl-1H-indol-5-yloxy)benzoic acid as white solid.

Workup

  1. stirringstirred at 50° C. for 30 minutes
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. additionwas added
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. washafter washed with water
  7. customa saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure
  8. additionHexane was added to the obtained residue
  9. customa solid substance was separated by filtration

Sources & evidence

ORD record
ord-728f6bc2f8764c59a1842267cca7f9c7
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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