4-Fluoro-3-methoxyaniline → HCID 23284662, compound

HRID 369266Notes

Reaction equation

HRID 369266 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]([Cl:30])[C:23]=1F)[C:16]([O:18][CH2:19][CH3:20])=[O:17])C.ClC1C(F)=C(C=C(F)C=1F)C(CC(OCC)=O)=O>C(Cl)(Cl)Cl>[Cl:30][C:24]1[C:25]([F:29])=[C:26]([F:28])[CH:27]=[C:22]2[C:23]=1[N:6]([C:5]1[CH:7]=[CH:8][C:2]([F:1])=[C:3]([O:9][CH3:10])[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 10934859Ethyl 3-(3-chloro-2,4,5-trifluorophenyl)-3-oxopropanoateHCID 54402571Ethyl 3-ethoxy-2-(3-chloro-2,4,5-trifluorobenzoyl)acrylate

Product 1

HCID 23284662HCID 23284662, 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) with ethyl 3-ethoxy-2-(3-chloro-2,4,5-trifluorobenzoyl)acrylate synthesized from ethyl 3-chloro-2,4,5-trifluorobenzoylacetate (2.8 g) in accordance with a method known per se in the art dissolved therein. The reaction mixture was concentrated under reduced pressure, and anhydrous potassium carbonate (2.7 g) and N,N-dimethylformamide (6 ml) were added to the residue, followed by stirring at 90° C. for 15 minutes. The reaction mixture was allowed to cool, and chloroform (80 ml) and distilled water (300 ml) were added to the reaction mixture, thereby conducting liquid separation. A chloroform layer was washed twice with distilled water (300 ml), dried over anhydrous magnesium sulfate and then 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 (2.98 g) as a colorless powder.

Workup

  1. dissolutiondissolved
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and anhydrous potassium carbonate (2.7 g) and N,N-dimethylformamide (6 ml)
  3. additionwere added to the residue
  4. temperatureto cool
  5. distillationchloroform (80 ml) and distilled water (300 ml)
  6. additionwere added to the reaction mixture
  7. customliquid separation
  8. washA chloroform layer was washed twice with distilled water (300 ml)
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. additionDeposits were dispersed in ethanol
  12. filtrationcollected by filtration
  13. washwashed with ethanol and diisopropyl ether in that order

Sources & evidence

ORD record
ord-7ea1afee1c1a40c4b8cd6bea0964e751
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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