Hydrochloric Acid → 2-Chloro-6-(methylamino)pyridine-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,6-dichloroisonicotinic acid (25 g, 130.2 mmol) in 52 mL water was added 60 mL of 40% methylamine in water. Reaction heated to reflux at 100° C. After 16 h, reaction was cooled to rt. Reaction was acidified with 1N HCl (200 mL) and extracted with EtOAc (300 mL×4). The combined organics were washed with brine (150 mL), dried over Mg2SO4, filtered, and concentrated in vacuo to give 24.2 g (100%) of 2-chloro-6-(methylamino)isonicotinic acid as a brown solid. LC/MS [M+H]+ 187.0.

Provenance & Evidence