tert-Butoxy bis(dimethylamino)methane → (E)-2-(2-(dimethylamino)vinyl)-4-nitrobenzonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-methyl-4-nitrobenzonitrile (Aldrich, 5.0 g, 31 mmol) and 1-(1,1-dimethylethoxy)-N,N,N′,N′-tetramethyl-methanediamine (Aldrich, 12.2 mL, 59 mmol) in dry DMF (8 mL) was stirred at 70° C. for 2 h under N2. After cooling to rt, DMF was removed in vacuo and the crude product was triturated with hexanes/ethyl acetate (5:1). The solid was collected by filtration and washed with hexane to give (E)-2-(2-(dimethylamino)vinyl)-4-nitrobenzonitrile (6.5 g, 97% yield) as a black solid. 1H NMR (400 MHz, CDCl3) δ ppm 2.97 (s, 6H) 5.36 (d, J=513.18 Hz, 1H) 7.16 (d, J=13.62 Hz, 1H) 7.52 (d, J=8.79 Hz, 1H) 7.60 (m, 1H) 8.11 (d, J=1.76 Hz, 1H).

Provenance & Evidence