2,5-Dichloronitrobenzene → 2-(4-Chloro-2-nitro-phenylamino)-5-isopropyl-benzonitrile

Participants

Reaction Conditions

Reaction Steps

Combine 1,4-dichloro-2-nitro-benzene (0.513 g, 2.67 mmol), 2-amino-5-isopropyl-benzonitrile (0.514 g, 3.21 mmol), potassium carbonate (0.754 g, 5.45 mmol), and fine granular copper (0.031 g, 0.48 mmol) in dimethylformamide (5 ml). Heat the reaction mixture to 160° C. for 16 hours, and cool to ambient temperature. Dilute the reaction mixture with 50 ml of ethyl acetate and wash 3 times with 50 ml water and once with 50 ml of brine. Collect organic layer, dry over sodium sulfate and evaporate solvent. Purify the residue via flash chromatography eluting with a step gradient starting with 90% hexanes: 10% ethyl acetate and going to 85% hexanes: 15% ethyl acetate to obtain 0.316 g (1.00 mmol, 37% yield) of the title compound as an orange amorphous solid: Mass Spectrum (m/e): 316 (M+1).

Provenance & Evidence