Triethylamine → HCID 21840838, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3,4-dimethoxy-6-(2-chloroisonicotinoyl)benzoic acid (70 g) in tetrahydrofuran (1800 ml) is added triethylamine (45.5 ml) at room temperature under nitrogen atmosphere, and thereto is added dropwise ethyl chloroformate (25 ml) at a temperature below -20° C., and the mixture is stirred at -20° C. for 10 minutes. To the reaction mixture is added a 1.38 M aqueous sodium azide solution (500 ml), and the mixture is stirred at room temperature for 1.5 hour, and extracted with ethyl acetate. The extract is washed, dried, and concentrated. The residue is dissolved in toluene (1300 ml), and the mixture is heated under reflux for one hour. To the reaction mixture is added conc. hydrochloric acid (450 ml) under ice-cooling, and the mixture is heated with stirring at 80° C. for one hour. To the reaction mixture is added ice-water, and the mixture is extracted with chloroform. The extract s washed, dried and concentrated. The residue is crystallized from ether to give 3,4-dimethoxy-6-(2-chloroisonicotinoyl)aniline (50.3 g).

Provenance & Evidence