4-Chloroaniline → HCID 58026182, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,6-dichloropyrazine (2.0 g, 13.4 mmol), 4-chloroaniline (1.88 g, 14.8 mmol) and sodium tert-butoxide (1.71 g, 17.6 mmol) in toluene (45 mL) were degassed with argon for 20 minutes. (±)-2,2′-Bis(diphenylphosphino-)1,1′-binaphthalene ((±)-BINAP) (502 mg, 0.81 mmol) and palladium(II)-acetate (90.4 mg, 0.40 mmol) were added followed by degassing for 5 minutes. The reaction mixture was stirred at 100° C. over night. The mixture was filtrated and the filtrate evaporated. Flash chromatography (ethyl acetate/heptane as eluent) gave (4-chloro-phenyl)-(6-chloro-pyrazin-2-yl)-amine (628 mg, 18%) as a brown oil.

Provenance & Evidence