Reaction #84483

Reaction equation

DCM

2-fluoro-5-nitrobenzonitrile

K2CO3

dihexylamine

→

title compound

Yield 87.4%

2-cyano-N,N-dihexyl-4-nitroaniline

Yield 87.4%

Solvents

CH3CN

Conditions

Workup

1. 1
   TemperatureThe mixture was cooled to rt
2. 2
   Washwashed with water (100 mL×3), brine (100 mL)
3. 3
   Dryingdried over anhydrous Na2SO4
4. 4
   Concentrationconcentrated in vacuo
5. 5
   OtherThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=125:2)

Procedure

To a solution of 2-fluoro-5-nitrobenzonitrile (1.83 g, 10.0 mmol) in CH3CN (20 mL) were added K2CO3 (2.76 g, 20.0 mmol) and dihexylamine (1.85 g, 9.98 mmol) and the mixture was stirred at 80° C. for 40 h. The mixture was cooled to rt, poured into 100 mL of DCM and washed with water (100 mL×3), brine (100 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=125:2) to give the title compound as yellow oil (2.89 g, 87%).

Source