4-Aminobenzonitrile → 4-Amino-3-chlorobenzonitrile

HRID 1087125Notes

Reaction equation

HRID 1087125 reaction equation
[C:1]([C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1)#[N:2].[Cl:10]N1C(=O)CCC1=O>C(#N)C>[Cl:10][C:5]1[CH:4]=[C:3]([C:1]#[N:2])[CH:9]=[CH:8][C:6]=1[NH2:7]

Participants

4

Reactant 2

HCID 133964-AminobenzonitrileHCID 31398Chlorosuccinimide2×

Product 1

HCID 5198964-Amino-3-chlorobenzonitrileYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred, 60° C. solution of 4-cyanoaniline (20 g, 0.169 mol) in acetonitrile (200 mL) was added slowly N-chlorosuccinimide (24.8 g, 0.186 mol) to keep the reaction at reflux. After the addition of the N-chlorosuccinimide was complete, the reaction mixture was stirred at 60° C. for two hours. The solvent was then removed under reduced pressure. The residue was then dissolved in dichloromethane, washed with a 5% sodium hydroxide solution, dried (Na2SO4) and evaporated under reduced pressure to afford 24.5 g (95%) of the title compound, 2-chloro-4-cyanoaniline, as a tan solid; m.p. 93°-95° C.

Workup

  1. customthe reaction
  2. temperatureat reflux
  3. customThe solvent was then removed under reduced pressure
  4. dissolutionThe residue was then dissolved in dichloromethane
  5. washwashed with a 5% sodium hydroxide solution
  6. dry with materialdried (Na2SO4)
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f515554437ee464e87f977c04f25c0c0
Source dataset
uspto-grants-1991_07
Patent number
US05034410

Reaction notes

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