4-Fluoro-3-methoxyaniline → HCID 23284696, compound

HRID 369247Notes

Reaction equation

HRID 369247 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[O:9][CH3:10].C(O[CH:14]=[C:15]([C:21](=[O:32])[C:22]1[CH:27]=[C:26]([F:28])[C:25]([F:29])=[C:24]([CH3:30])[C:23]=1F)[C:16]([O:18][CH2:19][CH3:20])=[O:17])C.F[C:34]1C(C)=C(F)C(F)=CC=1C(CC(OCC)=O)=O>C(Cl)(Cl)Cl>[F:28][C:26]1[CH:27]=[C:22]2[C:23](=[C:24]([CH3:30])[C:25]=1[F:29])[N:6]([C:5]1[CH:7]=[CH:8][C:2]([F:1])=[C:3]([O:9][CH2:10][CH3:34])[CH:4]=1)[CH:14]=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:21]2=[O:32]

Participants

5

Reactant 3

HCID 27745334-Fluoro-3-methoxyanilineHCID 14052572Ethyl 3-oxo-3-(2,4,5-trifluoro-3-methylphenyl)propanoateHCID 53656353HCID 53656353, compound

Product 1

HCID 23284696HCID 23284696, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
90 °C

Procedure

4-Fluoro-3-methoxyaniline (1.4 g) was added to a chloroform solution (10 ml) of ethyl 3-ethoxy-2-(2,4,5-trifluoro-3-methylbenzoyl)acrylate synthesized from ethyl 2,4,5-trifluoro-3-methylbenzoylacetate (2.6 g) in accordance with a method known per se in the art. The mixture was concentrated under reduced pressure, and anhydrous potassium carbonate (3.0 g) and N,N-dimethylformamide (7 ml) were added to the residue, followed by stirring at 90° C. for 15 minutes. The reaction mixture was allowed to cool, and chloroform (100 ml) and distilled water (250 ml) were added to the mixture, thereby conducting liquid separation. A chloroform layer was then washed twice with distilled water (250 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Deposits were dispersed in ethanol, collected by filtration and washed with ethanol and diisopropyl ether in that order to obtain the title compound (2.59 g) as a colorless powder.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure, and anhydrous potassium carbonate (3.0 g) and N,N-dimethylformamide (7 ml)
  2. additionwere added to the residue
  3. temperatureto cool
  4. distillationchloroform (100 ml) and distilled water (250 ml)
  5. additionwere added to the mixture
  6. customliquid separation
  7. washA chloroform layer was then washed twice with distilled water (250 ml)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. additionDeposits were dispersed in ethanol
  11. filtrationcollected by filtration
  12. washwashed with ethanol and diisopropyl ether in that order

Sources & evidence

ORD record
ord-a7ec8c2365cb461484695ae3ac638dbf
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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