Water → HCID 59261367, compound

Participants

Reaction Conditions

Reaction Steps

(E)-1-(2-chlorobenzylidene)hydrazine (0.351 g, 2.27 mmol), dichloro[1,1′bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (0.0185 g, 0.0227 mmol) and potassium carbonate (0.471 g, 3.41 mmol) was added to a 50-mL RBF. Toluene (2 mL) was added and 2,4-dichloro-6-methylpyridine (0.368 g, 2.27 mmol) in 3 mL of toluene was added. The red mixture was heated to 100° C. After 18 h, the reaction was allowed to cool to RT and water (20 mL) was added. The mixture was filtered and 190 mg of (E)-1-(2-chlorobenzylidene)-2-(4-chloro-6-methylpyridin-2-yl) hydrazine was collected as a tan solid. The filtrate was absorbed on silica gel and purified by silica gel chromatography (8/2 hexanes/DCM to 7/2/1 hexans/DCM/EtOAc) to afford an additional 200 mg of (E)-1-(2-chlorobenzylidene)-2-(4-chloro-6-methylpyridin-2-yl) hydrazine as a tan solid. MS (ESI, pos. ion) m/z: 280.0 (M+1).

Provenance & Evidence