Potassium Cyanide → 2-(4-Chlorophenyl)-4,5,6,7-tetrahydro-2h-indazol-3-amine

HRID 2419977Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2419977
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH2:9])=[CH:4][CH:3]=1.[C:10]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C:13]1=O)#[N:11].ClC1CCCCC1=O.[C-]#N.[K+]>C(O)(=O)C.C1(C)C=CC=CC=1.C(N(CC)CC)C>[NH2:11][C:10]1[N:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]=[C:13]2[C:12]=1[CH2:17][CH2:16][CH2:15][CH2:14]2

Komponenten

8

Edukt 4

HCID 9032Potassium CyanideHCID 132032-ChlorocyclohexanoneHCID 70624(4-Chlorophenyl)hydrazineHCID 2202972-Oxocyclohexanecarbonitrile

Produkt 1

HCID 203121732-(4-Chlorophenyl)-4,5,6,7-tetrahydro-2h-indazol-3-amine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidKatalysatorHCID 1140TolueneLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of 3.6 parts of 4-chlorophenylhydrazine and 2.0 parts of triethylamine in 20.0 parts of toluene was stirred at room temperature for fifteen minutes. To the mixture was added 2.5 parts of 2-cyanocyclohexanone, prepared from commercial 2-chlorocyclohexanone and potassium cyanide [von R. E. Meyer, Helv. Chim. Acta., 16, 1291 (1933)], and a few drops of acetic acid. After refluxing for 2 hours, followed by stirring at room temperature overnight, the reaction mixture was evaporated to remove toluene and was treated with water, extracted with diethyl ether, dried over anhydrous magnesium sulfate and concentrated. Recrystallization from ethanol/water gave 2.6 parts of the compound, m.p. 140°-142°.

Aufarbeitung

  1. temperatureAfter refluxing for 2 hours
  2. stirringby stirring at room temperature overnight
  3. customthe reaction mixture was evaporated
  4. customto remove toluene
  5. additionwas treated with water
  6. extractionextracted with diethyl ether
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customRecrystallization from ethanol/water
  10. customgave 2.6 parts of the compound, m.p. 140°-142°

Quellen und Nachweise

ORD-Eintrag
ord-8840b8dc260a4cfaa2724902b9ab9428
Quelldatensatz
uspto-grants-1978_08
Patentnummer
US04108628

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