Ethyl 2-oxocyclohexanecarboxylate → (2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-1,2,4,5,6,7-hexahydro-3H-indazol-3-one

HRID 21468

Reaktionsgleichung

Reaktionsgleichung von HRID 21468
[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][NH2:16].C([O:19][C:20]([CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][C:23]1=O)=O)C>C(O)(=O)C>[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[N:15]1[C:23]2[CH2:24][CH2:25][CH2:26][CH2:27][C:22]=2[C:20](=[O:19])[NH:16]1

Komponenten

4

Edukt 2

HCID 95543Ethyl 2-oxocyclohexanecarboxylateHCID 152793962-Fluoro-4-chloro-5cyclopentyloxyphenylhydrazine

Produkt 1

HCID 86748708(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-1,2,4,5,6,7-hexahydro-3H-indazol-3-oneAusbeute 72,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

2-Fluoro-4-chloro-5-cyclopentyloxyphenylhydrazine (24.5 g, 0.10 mol), 2-ethoxycarbonylcyclohexanone (17.0 g, 0.10 mol) were dissolved in acetic acid (200 ml), and stirred for 2 hours while heating under refluxing. After completion of the reaction, the solvent was distilled off to obtain a crude product (37 g). The product was washed with a mixed solvent of benzene/hexane to obtain 2N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-1,2,4,5,6,7-hexahydro-3H-indazol-3-one as a white solid (25.3 g, 72.3% yield)

Aufarbeitung

  1. temperaturewhile heating
  2. temperatureunder refluxing
  3. customAfter completion of the reaction
  4. distillationthe solvent was distilled off
  5. customto obtain a crude product (37 g)
  6. washThe product was washed with a mixed solvent of benzene/hexane

Quellen und Nachweise

ORD-Eintrag
ord-d09c4caf94244880bad4145de2e29eb2
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05424277

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