Isonicotinic Acid → N-Methoxy-N-methylisonicotinamide

Participants

Reaction Steps

To a suspension of 4-pyridinecarboxylic acid (12.3 g, 100 mmol) over CH2Cl2 (200 mL) a solution of CDI (18.0 g, 111 mmol) in CH2Cl2 (200 mL) was added. After addition, the mixture was stirred for 2 h at room temperature. Following this, N,O-dimethylhydroxyl-amine hydrochloride (13.9 g, 145 mmol) was added and the mixture was stirred overnight. The reaction mixture was quenched with 1N NaOH and the phases separated. The organic layer was dried over Na2SO4 and concentrated. The crude product was purified by column chromatography (PE/EtOAc=1:1) to give the title compound as orange oil (10.1 g, 61% yield). LC-MS (Method A): m/z 167 (M+H)+, Rt: 0.49 min. 1H NMR (400 MHz, CDCl3): δ=8.64 (d, J=6.0 Hz, 2H), 7.46 (d, J=6.0 Hz, 2H), 3.47 (s, 3H), 3.30 (s, 3H).

Provenance & Evidence