Acetic Acid → HCID 15591174, compound

HRID 255652Notes

Reaction equation

HRID 255652 reaction equation
[O:1]=[C:2]([CH:8]=[CH:9][C:10]1[NH:11][CH:12]=[CH:13][CH:14]=1)[CH2:3][C:4]([O:6]C)=[O:5].[OH:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1.Cl[C:24]1C(=O)C(Cl)=C(Cl)C(=O)C=1Cl.C(O)(=O)C>C1C=CC=CC=1.O1CCOCC1>[OH:15][C:16]1[CH:22]=[CH:21][C:19]([N:20]2[C:9]([C:10]3[NH:11][CH:12]=[CH:13][CH:14]=3)=[CH:8][C:2](=[O:1])[C:3]([C:4]([OH:6])=[O:5])=[CH:24]2)=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 4034-AminophenolHCID 8371ChloranilHCID 54286043HCID 54286043, compound

Product 1

HCID 15591174HCID 15591174, compoundYield 46.1%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 312751,4-DioxaneSolvent2×

Procedure

In 5 ml of benzene was dissolved 1 g of methyl 3-oxo-5-(pyrrol-2-yl)-4-pentenoate and to this solution was added 0.74 g of N,N-dimethylformamidodimethylacetal. They were reacted at 70° C. for 1.5 hours. To the reaction mixture was then added 0.56 g of 4-hydroxyaniline, and they were further reacted at room temperature for 1 hour. The precipitated crystals were collected by filtration and dissolved in 10 ml of N,N-dimethylformamide. They were reacted at 140° C. for 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and the solvent was removed by distillation under reduced pressure. 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 to this solution was added dropwise a solution of 0.54 g of 2,3,5,6-tetrachloro-p-benzoquinone in 5 ml of dioxane at 95° C. Thereafter, the mixture was subjected to reaction at the same temperature for 30 minutes, and the reaction mixture was cooled to room temperature. The precipitated crystals were collected by filtration, dissolved in a mixture of 5 ml of methanol and 10 ml of a 10% by weight aqueous sodium hydroxide solution, and they were reacted at room temperature for 30 minutes. After completion of the reaction, the reaction mixture 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 0.3 g of 1-(4-hydroxyphenyl)-4-oxo-6-(pyrrol-2-yl)-1,4-dihydronicotinic acid having a melting point of 250° C. or more.

Workup

  1. customThey were reacted at 70° C. for 1.5 hours
  2. customwere further reacted at room temperature for 1 hour
  3. filtrationThe precipitated crystals were collected by filtration
  4. dissolutiondissolved in 10 ml of N,N-dimethylformamide
  5. customThey were reacted at 140° C. for 3 hours
  6. customAfter completion of the reaction
  7. customthe solvent was removed by distillation under reduced pressure
  8. customThe residue was purified by a column chromatography (Wako Silica Gel C-200; eluent: chloroform)
  9. customto obtain an oily substance
  10. customThereafter, the mixture was subjected to reaction at the same temperature for 30 minutes
  11. temperaturethe reaction mixture was cooled to room temperature
  12. filtrationThe precipitated crystals were collected by filtration
  13. dissolutiondissolved in a mixture of 5 ml of methanol and 10 ml of a 10% by weight aqueous sodium hydroxide solution, and they
  14. customwere reacted at room temperature for 30 minutes
  15. customAfter completion of the reaction
  16. filtrationthe precipitated crystals were collected by filtration
  17. washwashed with water
  18. customdried

Sources & evidence

ORD record
ord-f64d00dcb6514e649ef37139cc6d8814
Source dataset
uspto-grants-1987_10
Patent number
US04698352

Reaction notes

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