Ethyl Acetate → (3-Methyl-4-nitro-1H-pyrazol-1-YL)acetonitrile

HRID 577743Notes

Reaction equation

HRID 577743 reaction equation
[CH3:1][C:2]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][NH:4][N:3]=1.Br[CH2:11][C:12]#[N:13].C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CN(C=O)C>[CH3:1][C:2]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][N:4]([CH2:11][C:12]#[N:13])[N:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 178434564HCID 178434564, compound

Product 1

HCID 19620685(3-Methyl-4-nitro-1H-pyrazol-1-YL)acetonitrileYield 38.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-methyl-4-nitro-1H-pyrazole (7 g, 0.055 mol), bromoacetonitrile (13.2 g, 0.11 mol) and K2CO3 (23 g, 0.165 mol) in DMF (120 mL) was stirred at 80° C. for 2 hrs. TLC (petroleum ether:EtOAc=2:1) showed the reaction was complete. The mixture was filtered, concentrated and the residue purified by flash chromatography (petroleum ether:EtOAc=4:1) to give the title compound (3.5 g, 38% yield) as light yellow oil.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customthe residue purified by flash chromatography (petroleum ether:EtOAc=4:1)

Sources & evidence

ORD record
ord-9963224fe4c54c54980093792cbabddb
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Reaction notes

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