Acetic Acid → HCID 15591125, compound

HRID 255641Notes

Reaction equation

HRID 255641 reaction equation
C1(C(C2C=CC=CC=2)[O:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[N:18]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[CH:19]=[C:20]([C:25](=[O:27])[CH:26]=3)[C:21]([O:23]C)=[O:22])=[CH:13][CH:12]=2)=[O:10])C=CC=CC=1.O.C1C=CC=CC=1.C(O)(=O)C>C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>[C:9]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:18]([C:28]3[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=3)[CH:19]=[C:20]([C:25](=[O:27])[CH:26]=2)[C:21]([OH:23])=[O:22])=[CH:13][CH:12]=1)([OH:10])=[O:8]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 241BenzeneHCID 962WaterHCID 15591003HCID 15591003, compound

Product 1

HCID 15591125HCID 15591125, compoundYield 60.4%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

In a mixed solvent of 2.5 ml of anisole and 2.5 ml of trifluoroacetic acid was dissolved 0.25 g of methyl 6-(4-diphenylmethyloxycarbonylphenyl)-1-(4-fluorophenyl)-4-oxo-1,4-dihydronicotinate, and they were reacted at room temperature for 1.5 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure, and the residue was dissolved in a mixed solvent of 2.5 ml of ethanol and 2.5 ml of a 1N aqueous sodium hydroxide solution, and the resulting solution was subjected to reaction at room temperature for 3 hours. After completion of the reaction, 20 ml of water and 20 ml of benzene were added to the reaction mixture and the aqueous layer was separated. The aqueous solution thus obtained was adjusted to a pH of 5.5 with acetic acid and the precipitated crystals were collected by filtration, to obtain 0.10 g of 6-(4-carboxyphenyl)-1-(4-fluorophenyl)-4-oxo-1,4-dihydronicotinic acid having a melting point of 280° C. or more.

Workup

  1. customwere reacted at room temperature for 1.5 hours
  2. customAfter completion of the reaction
  3. customthe solvent was removed by distillation under reduced pressure
  4. dissolutionthe residue was dissolved in a mixed solvent of 2.5 ml of ethanol and 2.5 ml of a 1N aqueous sodium hydroxide solution
  5. customthe resulting solution was subjected to reaction at room temperature for 3 hours
  6. additionwere added to the reaction mixture
  7. customthe aqueous layer was separated
  8. customThe aqueous solution thus obtained
  9. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-bb68ed8e21f6456b80b33c2786b63a79
Source dataset
uspto-grants-1987_10
Patent number
US04698352

Reaction notes

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