Potassium Carbonate → 5-amino-1-phenyl-1H-pyrazole-3-carbonitrile

HRID 522152Notes

Reaction equation

HRID 522152 reaction equation
C([C:3]([N:9]=[N:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH2:6][C:7]#[N:8])[C:4]#[N:5])C.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[NH2:8][C:7]1[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:9]=[C:3]([C:4]#[N:5])[CH:6]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 118497096Ethyl 2-(phenyldiazenyl)succinonitrile

Product 1

HCID 177636545-amino-1-phenyl-1H-pyrazole-3-carbonitrileYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 2-(phenyldiazenyl)succinonitrile (Preparation 55, 2.84 g, 15.43 mmol) in dichloromethane (103 mL) was added a 10% aqueous solution of potassium carbonate (77 mL, 55.71 mmol). The reaction was stirred at room temperature for 18 hours. The organic layer was separated dried over magnesium sulphate and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 0-3% MeOH in DCM to afford the title compound (1.24 g, 44%).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified
  5. washeluting with 0-3% MeOH in DCM

Sources & evidence

ORD record
ord-bfaac401d16045c5b41cdf1d7fa4c13b
Source dataset
uspto-grants-2016_05
Patent number
US09328096B2

Reaction notes

Loading…