Hydrochloric Acid → HCID 67813064, compound

Temperature

60 °C

Sodium methoxide (19 gm) was dissolved in methanol (610 ml) and then added 2,3-dimethyl-2H-indazol-6-amine (13 gm). The reaction mixture was stirred for 15 minutes and then added paraformaldehyde (3.9 gm). The contents were heated to 60° C. and stirred for 10 hours. The reaction mass was then cooled to room temperature and maintained for 4 hours 30 minutes. Sodium borohydride (2.8 gm) was added to the reaction mass slowly at room temperature and then heated to reflux. The reaction mass was maintained for 2 hours at reflux and then cooled to room temperature. The reaction mass was stirred for 14 hours at room temperature and then added sodium hydroxide solution (1M, 100 ml). The pH of the reaction mass was adjusted to 8.0 to 8.5 with hydrochloric acid solution (40 ml) and then added ethyl acetate (400 ml). Then the layers were separated and the aqueous layer was extracted with ethyl acetate. The organic layer was dried with sodium sulfate and treated with carbon. The combined organic layers were washed with sodium chloride solution and dried with sodium sulfate. The organic layer was treated with carbon and filtered through hi-flow bed. The solvent was distilled off under vacuum at below 50° C. to obtain a residual mass. To the residual mass was added diisopropyl ether (75 ml) and stirred for 1 hour, filtered. The solid obtained was dried to give 10 gm of N,2,3-trimethyl-2H-indazol-6-amine.

1. stirringstirred for 10 hours
2. temperatureThe reaction mass was then cooled to room temperature
3. temperaturemaintained for 4 hours 30 minutes
4. temperatureheated to reflux
5. temperatureThe reaction mass was maintained for 2 hours
6. temperatureat reflux
7. temperaturecooled to room temperature
8. stirringThe reaction mass was stirred for 14 hours at room temperature
9. customThen the layers were separated
10. extractionthe aqueous layer was extracted with ethyl acetate
11. dry with materialThe organic layer was dried with sodium sulfate
12. additiontreated with carbon
13. washThe combined organic layers were washed with sodium chloride solution
14. dry with materialdried with sodium sulfate
15. additionThe organic layer was treated with carbon
16. filtrationfiltered through hi-flow bed
17. distillationThe solvent was distilled off under vacuum at below 50° C.
18. customto obtain a residual mass
19. stirringstirred for 1 hour
20. filtrationfiltered
21. customThe solid obtained
22. customwas dried

ORD record

ord-765ebfd0f0e94946ad430e9eb81a5b09

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09150547B2