Sodium Nitrate → HCID 59518096, compound

Temperature

-15 °C

5-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylamine (2.74 g, 10.87 mmol) is suspended in hydrochloric acid (21.74 mL, 5N) and the solution is cooled to −15° C. in a brine/ice bath. Sodium nitrate (0.9 g, 13.04 mmol) in water (10 mL) is added slowly to the mixture. The reaction is allowed to stir at −15° C. for ten minutes after complete addition. Hexafluorophosphoric acid (5 mL, 21.74 mmol of a 60% wt. solution in water) is added slowly to the mixture. The resulting slurry is filtered, rinsed with cold water, methanol, and diethyl ether, and dried under vacuum. This solid is added in small portions to a round bottom containing acetic acid (10 mL) at 105° C. This solution is cooled to room temperature then treated with sodium hydroxide (25 mL, 5N) for 30 min. The pH of this solution is adjusted to 6 with hydrochloric acid, extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, then filtered and concentrated to provide the title product (2.2 g, 8.69 mmol).

1. additionafter complete addition
2. filtrationThe resulting slurry is filtered
3. washrinsed with cold water, methanol, and diethyl ether
4. customdried under vacuum
5. additionThis solid is added in small portions to a round
6. additionbottom containing acetic acid (10 mL) at 105° C
7. temperatureThis solution is cooled to room temperature
8. additionthen treated with sodium hydroxide (25 mL, 5N) for 30 min
9. extractionextracted with ethyl acetate
10. washwashed with brine
11. dry with materialdried over anhydrous sodium sulfate
12. filtrationfiltered
13. concentrationconcentrated

ORD record

ord-2d30d878306d42e89b70a90f59340821

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609892B2