benzyl N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)carbamate → 4-Chloro-5-(cyclopentyloxy)-2-fluorobenzenamine

HRID 128555

Reaktionsgleichung

Reaktionsgleichung von HRID 128555
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:4][C:3]=1[NH:15]C(=O)OCC1C=CC=CC=1.[H][H]>[Pd].C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:4][C:3]=1[NH2:15]

Komponenten

5

Edukt 2

HCID 19374482benzyl N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)carbamateHCID 178418361HCID 178418361, Verbindung2×

Produkt 1

HCID 152793894-Chloro-5-(cyclopentyloxy)-2-fluorobenzenamineAusbeute 99,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Benzyl N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)carbamate (2.00 g, 5.51 mmol) synthesized as described above, 5% Pd/C (100 mg) as a catalyst, and toluene (15 ml) as a solvent were charged into a 50 cc round-bottom flask, and the inside of the flask was replaced sufficiently with a hydrogen gas. Then, in a hydrogen gas atmosphere, the mixture was thoroughly stirred for 8 hours at 50° C. After completion of the reaction, the catalyst was separated by filtration, the resulting filtrate was dried with anhydrous magnesium sulfate. After separating the drying agent by filtration, the solvent was distilled off under reduced pressure from the filtrate to obtain quantitatively 2-fluoro-4-chloro-5cyclopentyloxyaniline (1.26 g) as a pale brown oily substance. The spectral data and the like are shown in Reference Example 1.

Aufarbeitung

  1. customAfter completion of the reaction
  2. customthe catalyst was separated by filtration
  3. dry with materialthe resulting filtrate was dried with anhydrous magnesium sulfate
  4. customAfter separating the drying agent
  5. filtrationby filtration
  6. distillationthe solvent was distilled off under reduced pressure from the filtrate

Quellen und Nachweise

ORD-Eintrag
ord-15fe274cba2f4116b90fd10b4beba6a7
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05464811

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