Hydrochloric Acid → HCID 57668049, compound

HRID 2191775Notes

Reaction equation

HRID 2191775 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][C:5]([NH:6][C:7]2[CH:19]=[C:18]([N:20]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:22]=[CH:21]3)[CH:17]=[CH:16][C:8]=2[C:9]([O:11]C(C)(C)C)=[O:10])=[CH:4][CH:3]=1.O1CCOCC1.[OH-].[Na+].Cl>C(OCC)(=O)C.O.CO>[F:1][C:2]1[CH:30]=[CH:29][C:5]([NH:6][C:7]2[CH:19]=[C:18]([N:20]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:22]=[CH:21]3)[CH:17]=[CH:16][C:8]=2[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 312751,4-DioxaneHCID 68959346HCID 68959346, compound

Product 1

HCID 57668049HCID 57668049, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

To the obtained tert-butyl 2-(4-fluoroanilino)-4-(1H-indol-1-yl)benzoate were added dioxane 1.5 mL, methanol 1.5 mL and 2.0 mol/L sodium hydroxide aqueous solution 0.41 mL, and it was stirred at 40° C. for 5 hours. After the reaction mixture was cooled to room temperature, 2.0 mol/L sodium hydroxide aqueous solution 0.41 mL was added to it, and it was stirred at 50° C. for 3 hours. After the reaction mixture was cooled to room temperature, water was added to it, it was adjusted to pH3.6 with 1.0 mol/L hydrochloric acid, and ethyl acetate was added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after sequential washing with water and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by reversed-phase silica gel column chromatography [eluent; 60-100% acetonitrile/0.1% trifluoroacetic acid aqueous solution] to give 2-(4-fluoroanilino)-4-(1H-indol-1-yl)benzoic acid 6.0 mg of a white solid.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. stirringwas stirred at 50° C. for 3 hours
  3. temperatureAfter the reaction mixture was cooled to room temperature
  4. additionwas added to it
  5. customThe organic layer was separated
  6. washafter sequential washing with water and saturated sodium chloride aqueous solution
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-90468a00b73049c387f7f8df67fe9d7c
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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