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

HRID 1439346Notes

Reaction equation

HRID 1439346 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Procedure

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 two 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°.

Workup

  1. temperatureAfter refluxing for two 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°

Sources & evidence

ORD record
ord-37a261251e604ed5adada10d7346342c
Source dataset
uspto-grants-1977_11
Patent number
US04059434

Reaction notes

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