Ethanol → 4-Chloro-5-(cyclopentyloxy)-2-fluorobenzenamine

HRID 275098

Reaktionsgleichung

Reaktionsgleichung von HRID 275098
[OH-].[Na+].C(O)C.[F:6][C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([O:14][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:9][C:8]=1[NH:20]C(=O)OC>O>[F:6][C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([O:14][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:9][C:8]=1[NH2:20]

Komponenten

5

Edukt 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 15766845methyl N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)carbamate

Produkt 1

HCID 152793894-Chloro-5-(cyclopentyloxy)-2-fluorobenzenamineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

2N sodium hydroxide aqueous solution (3.5 ml) was added to an ethanol solution (1.5 ml) of methyl N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)carbamate (1.507 g, 5.24 mmol), and the mixture was heated under reflux for 2 hours. After reaction, the reaction liquid was cooled to room temperature, water was added thereto, and this was extracted with ethyl acetate (20 ml×2). The organic layer was washed with water and saturated brine and then dried over anhydrous magnesium sulfate. The drying agent was taken out by filtration, and the solvent was removed by distillation under reduced pressure, to obtain 2-fluoro-4-chloro-5-cyclopentyloxyaniline (1.20 g, 5.22 mmol). Yield: ~100%.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customAfter reaction
  4. customthe reaction liquid
  5. extractionthis was extracted with ethyl acetate (20 ml×2)
  6. washThe organic layer was washed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe drying agent was taken out by filtration
  9. customthe solvent was removed by distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-76c0d1ed09184dc19b11d51e7b86c166
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05391807

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