Dimethylformamide diethylacetal → ethyl 3-(dimethylamino)-2-(2-oxopyridin-1(2H)-yl)acrylate

Participants

Reaction Steps

Combined ethyl 2-(2-oxopyridin-1(2H)-yl)acetate (500 mg, 2.76 mmol), 1,1-diethoxy-N,N-dimethylmethanamine (2031 mg, 13.80 mmol) and DMF (2 mL) and heated at 100° C. for 15 h. The reaction mixture was diluted with xylenes and concentrated onto Celite® then purified on a 30 g NH silica column (Moritex) eluted with 0 to 100% EtOAc in hexanes to give the title compound (551 mg, 85% yield) as a light yellow solid. MS m/z 237 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.13 (br. s., 3 H) 2.77 (br. s., 6 H) 3.94-4.08 (m, 2 H) 6.17 (td, J=6.7, 1.3 Hz, 1 H) 6.36 (dt, J=9.0, 1.1 Hz, 1 H) 7.35-7.45 (m, 2 H) 7.47 (s, 1 H).

Provenance & Evidence