P-Anisidine → HCID 23359023, compound

HRID 1788665Notes

Reaction equation

HRID 1788665 reaction equation
F[C:2]1[C:19]([F:20])=[C:18]([F:21])[C:17]([F:22])=[CH:16][C:3]=1[C:4]([C:6](=[CH:12]OCC)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=1>C(O)C>[F:22][C:17]1[CH:16]=[C:3]2[C:2](=[C:19]([F:20])[C:18]=1[F:21])[N:31]([C:28]1[CH:29]=[CH:30][C:25]([O:24][CH3:23])=[CH:26][CH:27]=1)[CH:12]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:4]2=[O:5]

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 54346083Ethyl 3-ethoxy-2-(2,3,4,5-tetrafluorobenzoyl)acrylate

Product 1

HCID 23359023HCID 23359023, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 2-(2,3,4,5-tetrafluorobenzoyl)-3-ethoxyacrylate (0.4 g), p-anisidine (0.15 g) and ethanol (4 ml) is stirred at room temperature for 30 minutes. After the reaction, the solvent is distilled off under reduced pressure. To the resulting residue is added anhydrous dioxane (10 ml) and further added portionwise 60% sodium hydride (60 mg). The mixture is stirred at room temperature for 30 minutes. Thereafter, the reaction mixture is poured into saturated aqueous ammonium chloride and then extracted with dichloromethane to give ethyl 6,7,8-trifluoro-1-(4-methoxyphenyl)- 1,4-dihydro-4-oxoquinoline-3-carboxylate (0.37 g).

Workup

  1. customAfter the reaction
  2. distillationthe solvent is distilled off under reduced pressure
  3. additionTo the resulting residue is added anhydrous dioxane (10 ml)
  4. additionfurther added portionwise 60% sodium hydride (60 mg)
  5. stirringThe mixture is stirred at room temperature for 30 minutes
  6. additionThereafter, the reaction mixture is poured into saturated aqueous ammonium chloride
  7. extractionextracted with dichloromethane

Sources & evidence

ORD record
ord-a9304fd128cd465193acaec345266e54
Source dataset
uspto-grants-1987_08
Patent number
US04684648

Reaction notes

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