Ethyl Acetate → Methyl 5-(dimethylamino)nicotinate

Participants

Reaction Steps

To a stirring solution of 283 mg (1.86 mmol) of methyl 5-aminonicotinate in 19 mL of CH3CN and 19 mL of 37% formaldehyde in H2O was added 353 mg (5.62 mmol) of NaCNBH3, and 50 drops of acetic acid. The solution was stirred at r.t. for 18.5 h and 40 mL of EtOAc and 40 mL of sat. NaHCO3 solution was added. The layers were separated, and the organic layer was washed with 25 mL of sat. NaHCO3 and 25 mL of brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (0.5% MeOH/CHCl3) resulted in 124 mg of methyl 5-(dimethylamino)nicotinate as a yellow oil in 37% yield.

Provenance & Evidence