Ethyl Acetate → HCID 57668098, compound

HRID 2191797Notes

Reaction equation

HRID 2191797 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]1[CH:23]=[CH:22][C:14]([C:15]([O:17]C(C)(C)C)=[O:16])=[C:13]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH:12]=1.C(OCC)(=O)C>[C].[Pd].CO>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]1[CH:23]=[CH:22][C:14]([C:15]([OH:17])=[O:16])=[C:13]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH:12]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 68957343HCID 68957343, compound

Product 1

HCID 57668098HCID 57668098, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To the obtained tert-butyl 4-((E)-2-(2,3-dimethylphenyl)vinyl)-2-(4-fluoroanilino)benzoate were added ethyl acetate 1.5 mL, methanol 1.5 mL and 10% palladium-carbon 27 mg sequentially, and it was stirred under hydrogen atmosphere at room temperature for 3 hours and 20 minutes. The solvent was removed under reduced pressure after insoluble matter was filtrated. Dichloromethane 1.0 mL and trifluoroacetic acid 7.5 mL were added to the obtained residue, and it was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure,diisopropyl ether was added to the obtained residue, and solid matter was filtrated to give 4-(2-(2,3-dimethylphenyl)ethyl)-2-(4-fluoroanilino)benzoic acid 17 mg of a white solid.

Workup

  1. customThe solvent was removed under reduced pressure after insoluble matter
  2. filtrationwas filtrated
  3. additionDichloromethane 1.0 mL and trifluoroacetic acid 7.5 mL were added to the obtained residue, and it
  4. stirringwas stirred at room temperature for 2 hours
  5. customThe solvent was removed under reduced pressure,diisopropyl ether
  6. additionwas added to the obtained residue, and solid matter
  7. filtrationwas filtrated

Sources & evidence

ORD record
ord-7ceb81506f7447fbaa67e17ce79f07a8
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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