Water → 2-amino-5-bromo-N-(5-chloro-2-pyridyl)-3-hydroxybenzamide

Temperature

-15 °C

2-Amino-N-(5-chloro-2-pyridyl)-3-hydroxybenzamide (5.27 g) was dissolved in 60 ml of N,N-dimethylformamide and the solution was stirred at −15° C. N-Bromosuccinimide (3.56 g) was added thereto by dividing into four with an interval of 5 minutes each and the mixture was stirred at −15° C. for 1.5 hours. Then more 0.36 g of N-bromosuccinimide was added thereto, the mixture was stirred at −15° C. for 2 hours, then 120 ml of water and 120 ml of ethyl acetate were added thereto and the mixture was stirred at room temperature for 10 minutes. The resulting precipitate was filtered through Celite and an organic layer in the filtrate was collected while an aqueous layer was further extracted with ethyl acetate. Active carbon powder (2.6 g) was added to the resulting organic layer and the mixture was stirred for 15 minutes and filtered through Celite. The filtrate was washed with water and dried over anhydrous sodium sulfate, the solvent was evaporated in vacuo and the residue was dried to give 5.70 g of 2-amino-5-bromo-N-(5-chloro-2-pyridyl)-3-hydroxybenzamide.

1. customby dividing into four with an interval of 5 minutes
2. stirringwas stirred at −15° C. for 1.5 hours
3. stirringthe mixture was stirred at −15° C. for 2 hours
4. stirringthe mixture was stirred at room temperature for 10 minutes
5. filtrationThe resulting precipitate was filtered through Celite
6. customan organic layer in the filtrate was collected while an aqueous layer
7. extractionwas further extracted with ethyl acetate
8. additionActive carbon powder (2.6 g) was added to the resulting organic layer
9. stirringthe mixture was stirred for 15 minutes
10. filtrationfiltered through Celite
11. washThe filtrate was washed with water
12. dry with materialdried over anhydrous sodium sulfate
13. customthe solvent was evaporated in vacuo
14. customthe residue was dried

ORD record

ord-cf54cf6e6afe4726b96c5a998dd415b6

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07504417B2