Acetic Acid → 4'-Formyl-3'-(trifluoromethyl)-1,1'-biphenyl-3-carboxamide

HRID 70330Notes

Reaction equation

HRID 70330 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([NH2:20])=[O:19])[CH:13]=2)=[CH:8][C:7]=1[C:21]([F:24])([F:23])[F:22].CC(O)=O.C([O-])(O)=O.[Na+]>O>[CH:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([NH2:20])=[O:19])[CH:13]=2)=[CH:8][C:7]=1[C:21]([F:22])([F:23])[F:24])=[O:1]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 671599944'-(1,3-Dioxolan-2-yl)-3'-(trifluoromethyl)-3-biphenylcarboxamide

Product 1

HCID 582764304'-Formyl-3'-(trifluoromethyl)-1,1'-biphenyl-3-carboxamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

4′-(1,3-Dioxolan-2-yl)-3′-(trifluoromethyl)-1,1′-biphenyl-3-carboxamide (0.177 g; 0.525 mmol) was added to a solution of HOAc (4 mL) and water (1 mL) and the mixture was stirred at 65° C. in a sealed vial for 1 h. Upon cooling, the mixture was poured into satd NaHCO3 and extracted with EtOAc (×3). Combined organics were washed (water, brine), dried over Na2SO4 and concentrated in vacuo affording the title compound, which was used without further purification.

Workup

  1. temperatureUpon cooling
  2. extractionextracted with EtOAc (×3)
  3. washCombined organics were washed (water, brine)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b3fc81529bfa43a596870db83e38eceb
Source dataset
uspto-grants-2014_09
Patent number
US08822518B2

Reaction notes

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