Hydrazine → HCID 178441977, compound

HRID 2280411Notes

Reaction equation

HRID 2280411 reaction equation
[NH2:1][NH2:2].[F:3][CH:4]([C:7](=O)[C:8]([CH3:11])([CH3:10])[CH3:9])[C:5]#[N:6]>C(O)C>[C:8]([C:7]1[C:4]([F:3])=[C:5]([NH2:6])[NH:2][N:1]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 18368932HCID 18368932, compound

Product 1

HCID 178441977HCID 178441977, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine (1.29 g, 2.4 equiv) was added to a solution of 2-fluoro-4,4-dimethyl-3-oxopentanenitrile (2.40 g, 1 equiv) in ethanol (EtOH) (50 mL), and the reaction was heated at reflux overnight. The solvent was removed under reduced pressure, and the residue was dissolved in dichloromethane (DCM) and washed with water. The organic solution was dried over sodium sulfate and concentrated in vacuo to provide the title compound (1.43 g, 54% yield) which was used in the next reaction without purification.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux overnight
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in dichloromethane (DCM)
  5. washwashed with water
  6. dry with materialThe organic solution was dried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c91f4378cb6e40299fce1a43ae307308
Source dataset
uspto-grants-2015_09
Patent number
US09139532B2

Reaction notes

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