Potassium Cyanide → HCID 178510898, compound

HRID 436210

Reaction equation

HRID 436210 reaction equation
Cl[CH2:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[CH:10]=2)[NH:5][N:4]=1.[C-:13]#[N:14].[K+]>C(O)C.O>[C:13]([CH2:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[CH:10]=2)[NH:5][N:4]=1)#[N:14]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 178478451HCID 178478451, compound

Product 1

HCID 178510898HCID 178510898, compoundYield 69.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 3-chloromethyl-5-chloro-1H-indazole (4.5 g) in ethanol (50 ml) is dropwise added to a solution of potassium cyanide (17 g) in water (10 ml) while stirring at 5° C, and the resulting mixture is stirred at room temperature for 2 hours and at 50° C for 2 hours. The reaction mixture is cooled and the precipitated potassium chloride is removed by filtration. The filtrate is concentrated under reduced pressure, admixed with water and extracted with ether. The ether layer is washed with water, dried over anhydrous magnesium sulfate and concentrated to give 3-cyanomethyl-5-chloro-1H-indazole (3.0 g) as resinous material.

Workup

  1. stirringthe resulting mixture is stirred at room temperature for 2 hours and at 50° C for 2 hours
  2. temperatureThe reaction mixture is cooled
  3. customthe precipitated potassium chloride is removed by filtration
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. extractionextracted with ether
  6. washThe ether layer is washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b592167866d14dcd8943918814b4694a
Source dataset
uspto-grants-1977_02
Patent number
US04008070

Linked notes

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