Acetic Acid → HCID 13682570, compound

HRID 255669Notes

Reaction equation

HRID 255669 reaction equation
[C:1]1([CH:6]=[CH:7][C:8](=[O:24])[C:9](=[CH:14][NH:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][C:17]=2[CH3:23])[C:10]([O:12]C)=[O:11])[CH2:5][CH2:4][CH2:3][CH:2]=1.ClC1C(=O)C(Cl)=C(Cl)C(=O)C=1Cl.C(O)(=O)C>CN(C)C=O.O1CCOCC1>[C:1]1([C:6]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][C:17]=3[CH3:23])[CH:14]=[C:9]([C:8](=[O:24])[CH:7]=2)[C:10]([OH:12])=[O:11])[CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8371ChloranilHCID 178500766HCID 178500766, compound

Product 1

HCID 13682570HCID 13682570, compoundYield 195.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

In 5 ml of N,N-dimethylformamide was dissolved 0.7 g of methyl 5-(cyclopenten-1-yl)-2-(4-hydroxy-2-methylphenylaminomethylene)-3-oxo-4-pentenoate, and they were 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 substance was dissolved in 10 ml of dioxane, and 0.5 g of 2,3,5,6-tetrachloro-p-benzoquinone was added thereto. They were reacted at 80° C. for 30 minutes. The reaction mixture was cooled to room temperature, and the precipitated crystals were collected by filtration, and washed with 5 ml of dioxane. These crystals were dissolved in a mixture of 5 ml of methanol and 5 ml of a 1N aqueous sodium hydroxide solution, the resulting mixture was subjected to reaction at room temperature for 30 minutes. The reaction mixture was adjusted to a pH of 5.5 with acetic acid and the precipitated crystals were collected by filtration, washed with water, and dried to obtain 1.3 g of 6-(cyclopenten-1-yl)-1-(4-hydroxy-2-methylphenyl)-4-oxo-1,4-dihydronicotinic acid having a melting point of 211°-213° C.

Workup

  1. customwere 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. customThey were reacted at 80° C. for 30 minutes
  7. filtrationthe precipitated crystals were collected by filtration
  8. washwashed with 5 ml of dioxane
  9. dissolutionThese crystals were dissolved in a mixture of 5 ml of methanol and 5 ml of a 1N aqueous sodium hydroxide solution
  10. customthe resulting mixture was subjected to reaction at room temperature for 30 minutes
  11. filtrationthe precipitated crystals were collected by filtration
  12. washwashed with water
  13. customdried

Sources & evidence

ORD record
ord-330182dffa60415c861c937e750977ee
Source dataset
uspto-grants-1987_10
Patent number
US04698352

Reaction notes

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