P-Anisidine → HCID 23359023, compound

HRID 845026Notes

Reaction equation

HRID 845026 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 residue is added anhydrous dioxane (10 ml) and thereto is further added portionwise 60% sodium hydride (60 mg). The mixture is stirred at room temperature for 30 minutes. The reaction mixture is poured into saturated aqueous ammonium chloride, and the mixture is 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 residue is added anhydrous dioxane (10 ml)
  4. additionis further added portionwise 60% sodium hydride (60 mg)
  5. stirringThe mixture is stirred at room temperature for 30 minutes
  6. additionThe reaction mixture is poured into saturated aqueous ammonium chloride
  7. extractionthe mixture is extracted with dichloromethane

Sources & evidence

ORD record
ord-3f47cba2e3654375bef6823e0c5e7c91
Source dataset
uspto-grants-1988_07
Patent number
US04755513

Reaction notes

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