Sodium hydride → 3-Nitro-4-(propylamino)benzonitrile

HRID 348770Notes

Reaction equation

HRID 348770 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[NH2:12])[C:7]#[N:8])([O-:3])=[O:2].[H-].[Na+].I[CH2:16][CH2:17][CH3:18]>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[NH:12][CH2:16][CH2:17][CH3:18])[C:7]#[N:8])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 5959014-Amino-3-nitrobenzonitrile

Product 1

HCID 230793333-Nitro-4-(propylamino)benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (15 ml), 3-nitro-4-aminobenzonitrile (500 mg) was dissolved, and the solution was added with sodium hydride (135 mg), followed by stirring at room temperature for 9 hours. The solution was added with 1-iodopropane (328 ml) and stirred overnight at room temperature. After completion of the reaction, the solvent was distilled off under reduced pressure and the residue was then dissolved in chloroform. The solution was washed with water and then subjected to extraction with chloroform. The organic layer was washed with saturated saline solution and dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure and the residue was then purified through silica gel column chromatography (chloroform), thereby obtaining the subject compound (362 mg) as a white solid.

Workup

  1. stirringstirred overnight at room temperature
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure
  4. dissolutionthe residue was then dissolved in chloroform
  5. washThe solution was washed with water
  6. extractionsubjected to extraction with chloroform
  7. washThe organic layer was washed with saturated saline solution
  8. dry with materialdried with anhydrous sodium sulfate
  9. filtrationAfter filtration
  10. distillationthe solvent was distilled off under reduced pressure
  11. customthe residue was then purified through silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-bd81120ac3494919b155d95658a1dd97
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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