Sodium Cyanide → HCID 86694684, compound

HRID 475075Notes

Reaction equation

HRID 475075 reaction equation
Br[CH2:2][CH2:3][C:4]1[NH:8][N:7]=[C:6]([NH2:9])[CH:5]=1.[C-:10]#[N:11].[Na+]>C(#N)C.O>[NH2:9][C:6]1[CH:5]=[C:4]([CH2:3][CH2:2][C:10]#[N:11])[NH:8][N:7]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 86694683HCID 86694683, compound

Product 1

HCID 86694684HCID 86694684, compoundYield 60.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
-70 °C

Procedure

To a solution of 5-(2-bromoethyl)-1H-pyrazol-3-amine (9.3 g, 48.9 mmol.) in acetonitrile (100 mL) was added a solution of NaCN (2.88 g, 58.6 mmol) in water (3 mL). The reaction mixture was stirred at −70° C. for 16 h and then concentrated in vacuo to remove the solvent. The residue was partitioned between DCM and brine. The organic layer was dried (Na2SO4) and then concentrated in vacuo. The crude material was crystallized from MeOH-EtOAc to afford 4 g (60%) of 3-(3-amino-1H-pyrazol-5-yl)propanenitrile (87) as a yellow solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customto remove the solvent
  3. customThe residue was partitioned between DCM and brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude material was crystallized from MeOH-EtOAc

Sources & evidence

ORD record
ord-77a0aef88622462b92ab08810ce91b86
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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