Acetic Acid → HCID 15591099, compound

HRID 255638Notes

Reaction equation

HRID 255638 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]=[C:10]([C:15](=[O:28])[CH:16]=[CH:17][C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25]([CH3:27])=[O:26])=[CH:20][CH:19]=2)[C:11]([O:13]C)=[O:12])=[CH:4][CH:3]=1.ClC1C(=O)C(Cl)=C(Cl)C(=O)C=1Cl.C(O)(=O)C>CN(C)C=O.C1C=CC=CC=1>[NH:24]([C:21]1[CH:22]=[CH:23][C:18]([C:17]2[N:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH:9]=[C:10]([C:15](=[O:28])[CH:16]=2)[C:11]([OH:13])=[O:12])=[CH:19][CH:20]=1)[C:25]([CH3:27])=[O:26]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8371ChloranilHCID 178500763HCID 178500763, compound

Product 1

HCID 15591099HCID 15591099, compoundYield 82.8%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 6228DimethylformamideSolvent

Procedure

In 25 ml of N,N-dimethylformamide was dissolved 2.9 g of methyl 2-(4-fluorophenylaminomethylene)-5-(4-acetaminophenyl)-3-oxo-4-pentenoate, and they are reacted at 140° C. for 2 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure and the residue was purified by a column chromatography (Wako Silica Gel C-200; eluent: chloroform) to obtain an oily substance. This oily sugstance was dissolved in 30 ml of benzene, followed by dropwise addition thereto of a solution of 2.06 g of 2,3,5,6-tetrachloro-p-benzoquinone in 18 ml of benzene at 80° C. After completion of this dropwise addition, the reaction mixture was cooled to room temperature, and the precipitated crystals were collected by filtration and washed with 30 ml of benzene. These crystals were then dissolved in a mixed solution of 20 ml of methanol and 20 ml of a 1N aqueous sodium hydroxide solution, and they were reacted at room temperature for 30 minutes. The reaction solution was adjusted to a pH of 6.0 with acetic acid and the precipitated crystals were collected by filtration, washed with water and dried to obtain 2.3 g of 6-(4-acetaminophenyl)-1-(4-fluorophenyl)-4-oxo-1,4-dihydronicotinic acid having a melting point of 249°-250° C.

Workup

  1. customare reacted at 140° C. for 2 hours
  2. customAfter completion of the reaction
  3. customthe solvent was removed by distillation under reduced pressure
  4. customthe residue was purified by a column chromatography (Wako Silica Gel C-200; eluent: chloroform)
  5. customto obtain an oily substance
  6. additionfollowed by dropwise addition
  7. customat 80° C
  8. additionAfter completion of this dropwise addition
  9. filtrationthe precipitated crystals were collected by filtration
  10. washwashed with 30 ml of benzene
  11. dissolutionThese crystals were then dissolved in a mixed solution of 20 ml of methanol and 20 ml of a 1N aqueous sodium hydroxide solution, and they
  12. customwere reacted at room temperature for 30 minutes
  13. filtrationthe precipitated crystals were collected by filtration
  14. washwashed with water
  15. customdried

Sources & evidence

ORD record
ord-398b7a693e0642b1aae0ab79574f7472
Source dataset
uspto-grants-1987_10
Patent number
US04698352

Reaction notes

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