Water → 4-[(4-Methoxy-2-methylphenyl)amino]butanenitrile

Participants

Reaction Conditions

Reaction Steps

A solution of DIPEA (39 mL, 1 eq) and 4-methoxy-2-methylaniline (30 g, 0.22 mol) in anh. DMF (90 mL), under N2, was heated at 100° C. 4-Bromobutanenitrile (21 mL, 1 eq) was added dropwise. The internal temperature was raised to 110° C. and the reaction mixture was stirred for 2 hr. The mixture was cooled down to r.t. and diluted with MTBE (240 mL). Water (270 mL) was added and the phases were separated. The organic layer was further washed with water (150 mL) and evaporated to 150 mL. Fresh MTBE (150 mL) was added and the mixture again evaporated to 150 mL. The mixture was treated with cHex (540 mL) over 20 min and the resulting suspension left at room temperature for 1.5 hr. The suspension was filtered and the cake washed with a mixture MTBE (30 mL)/cHex (90 mL). The title compound was collected as a violet solid (23.8 g, 53%).

Provenance & Evidence