Hydrochloric Acid → HCID 57668001, compound

HRID 2191671Notes

Reaction equation

HRID 2191671 reaction equation
Cl.[C:2]([C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[C:12]([N:19]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)C(=O)C)[CH:11]=1)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>O1CCOCC1>[C:2]([C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[C:12]([NH:19][C:23]2[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=2)[CH:11]=1)(=[O:9])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 57667943HCID 57667943, compound

Product 1

HCID 57668001HCID 57668001, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

6.0 mol/L Hydrochloric acid 2.0 mL was added to dioxane 2.0 mL solution of 4-benzoyl-2-(N-(4-fluorophenyl)acetamido)benzoic acid 0.39 g, and it was heated and refluxed for 2 hours and 30 minutes. After the reaction mixture was cooled to room temperature, 6.0 mol/L hydrochloric acid 1.0 mL was added to it, and it was heated and refluxed for 4 hours. After the reaction mixture was cooled to room temperature, the solvent was removed under reduced pressure, and ethyl acetate and 1.0 mol/L hydrochloric acid were added to it. The organic layer was separated and collected, dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [eluent; chloroform:methanol:acetic acid=20:1:1] to give 4-benzoyl-2-(4-fluoroanilino)benzoic acid 0.27 g of yellow solid.

Workup

  1. temperaturewas heated
  2. temperaturerefluxed for 2 hours and 30 minutes
  3. temperaturewas heated
  4. temperaturerefluxed for 4 hours
  5. temperatureAfter the reaction mixture was cooled to room temperature
  6. customthe solvent was removed under reduced pressure, and ethyl acetate and 1.0 mol/L hydrochloric acid
  7. additionwere added to it
  8. customThe organic layer was separated
  9. customcollected
  10. dry with materialdried over anhydrous magnesium sulfate
  11. washafter washing with saturated sodium chloride aqueous solution
  12. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4f41b5b276dd40868bb384a815eecb5b
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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