Methanol → HCID 57668058, compound

HRID 2191763Notes

Reaction equation

HRID 2191763 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][C:5]([NH:6][C:7]2[CH:19]=[C:18]([C:20]3[CH:28]=[CH:27][CH:26]=[C:25]4[C:21]=3[CH:22]=[CH:23][NH:24]4)[CH:17]=[CH:16][C:8]=2[C:9]([O:11]C(C)(C)C)=[O:10])=[CH:4][CH:3]=1.CO.[OH-].[Na+].C1(C)C=CC=CC=1>O>[F:1][C:2]1[CH:30]=[CH:29][C:5]([NH:6][C:7]2[CH:19]=[C:18]([C:20]3[CH:28]=[CH:27][CH:26]=[C:25]4[C:21]=3[CH:22]=[CH:23][NH:24]4)[CH:17]=[CH:16][C:8]=2[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 1140TolueneHCID 14798Sodium Hydroxide3×HCID 68960712HCID 68960712, compound

Product 1

HCID 57668058HCID 57668058, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To the obtained tert-butyl 2-(4-fluoroanilino)-4-(1H-indol-4-yl)benzoate were added methanol 1.0 mL,dioxane 1.0 mL and 2.0 mol/L sodium hydroxide aqueous solution 0.23 mL, it was stirred at 50° C. for 2 hours and 30 minutes, subsequently 2.0 mol/L sodium hydroxide aqueous solution 0.23 mL was added, it was stirred at 50° C. for 4 hours, furthermore 2.0 mol/L sodium hydroxide aqueous solution 0.23 mL was added, and it was heated and refluxed for 2 hours. After the reaction mixture was cooled to room temperature, toluene and water were added to it. The water layer was separated and collected, it was adjusted to pH3.0 with 1.0 mol/L hydrochloric acid after washing with toluene, and ethyl acetate was added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. Diisopropyl ether was added to the obtained residue, and solid matter was filtrated to give 2-(4-fluoroanilino)-4-(1H-indol-4-yl)benzoic acid 23 mg of a yellow solid.

Workup

  1. stirringit was stirred at 50° C. for 4 hours
  2. temperatureit was heated
  3. temperaturerefluxed for 2 hours
  4. temperatureAfter the reaction mixture was cooled to room temperature
  5. customThe water layer was separated
  6. customcollected
  7. washafter washing with toluene, and ethyl acetate
  8. additionwas added to it
  9. customThe organic layer was separated
  10. washafter washing with saturated sodium chloride aqueous solution
  11. customthe solvent was removed under reduced pressure
  12. additionDiisopropyl ether was added to the obtained residue, and solid matter
  13. filtrationwas filtrated

Sources & evidence

ORD record
ord-2329ec8028e94fa099be9348ad701cdb
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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