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

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-methyl-4-nitrobenzonitrile (5.0 g, 31 mmol) and tert-butoxybis(dimethylamino)methane (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/EtOAc (5:1). The solid was collected by filtration and washed with hexane to give Intermediate 1A (6.5 g, 97%) as black solid. 1H NMR (400 MHz, CDCl3) δ 2.97 (s, 6H), 5.36 (d, J=13.2 Hz, 1H), 7.16 (d, J=13.6 Hz, 1H), 7.52 (d, J=8.8 Hz, 1H), 7.60 (m, 1H), 8.11 (d, J=1.8 Hz, 1H).

Provenance & Evidence