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

HRID 2080722Notes

Reaction equation

HRID 2080722 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 (20 ml), 3-nitro-4-aminobenzonitrile (1.12 g) was dissolved, and the solution was added with 60% sodium hydride (411 mg), followed by stirring at room temperature for 30 minutes. The solution was added with 1-iodopropane (805 μl) and stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure and the residue was then dissolved in ethyl acetate. The resultant was washed with water and then subjected to extraction with ethyl acetate. The organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate.

Workup

  1. stirringstirred at room temperature for 1 hour
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure
  4. dissolutionthe residue was then dissolved in ethyl acetate
  5. washThe resultant was washed with water
  6. extractionsubjected to extraction with ethyl acetate
  7. washThe organic layer was washed with a saturated saline solution
  8. dry with materialdried with anhydrous sodium sulfate

Sources & evidence

ORD record
ord-c9587ddeaa4a480097cc93df5ab3d27b
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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