Acetonitrile → 6-Chloro-2-[(2-methoxy-ethyl)-methyl-amino]-nicotinamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,6-dichloro-nicotinamide (1) (10 g, 52.9 mmol) in acetonitrile (anhydrous, 200 mL) was added (2-methoxy-ethyl)-methyl-amine (2) (18.8 g, 212 mmol). The reaction was heated at 60° C. for 1.5 hours. 5% NaOH solution (1000 mL) was slowly added. The solution was then extracted with EtOAc (3×250 mL). The combined organic layer was dried over MgSO4, filtered, and evaporated in vacuo. Purification was accomplished by silica gel chromatography, eluting with 5%-30% EtOAc/hexanes gradient, to afford 11.66 g (91% yield) of the title compound. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.07 (d, J=8.6 Hz, 1H), 7.76 (br. s., 1 H), 6.93 (d, J=8.2 Hz, 1 H), 5.66 (br. s., 1 H), 3.66-3.51 (m, 4 H), 3.32 (s, 3 H), 2.93 (s, 3 H).

Provenance & Evidence