Triethylamine → HCID 21840838, compound

Temperature

-20 °C

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).

1. stirringthe mixture is stirred at room temperature for 1.5 hour
2. extractionextracted with ethyl acetate
3. washThe extract is washed
4. customdried
5. concentrationconcentrated
6. dissolutionThe residue is dissolved in toluene (1300 ml)
7. temperaturethe mixture is heated
8. temperatureunder reflux for one hour
9. additionTo the reaction mixture is added conc. hydrochloric acid (450 ml) under ice-
10. temperaturecooling
11. temperaturethe mixture is heated
12. stirringwith stirring at 80° C. for one hour
13. additionTo the reaction mixture is added ice-water
14. extractionthe mixture is extracted with chloroform
15. washThe extract s washed
16. customdried
17. concentrationconcentrated
18. customThe residue is crystallized from ether

ORD record

ord-9ecbe5df127549639d9567c3c125ae5b

Source dataset

uspto-grants-1999_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05965730