Ammonia → 6-Methyl-2,4-bis(2,2,2-trifluoroethoxy)pyridin-3-amine

Temperature

80 °C

2,4-Bis(2,2,2-trifluoroethoxy)-6-methyl-3-nitropyridine (45.00 g, 134.7 mmol) was dissolved in isopropanol (300 mL). While stirring the solution at 80° C., a solution of sodium dithionite (78.00 g, 448.0 mmol) in water (300 mL) was added, followed by stirring for 15 minutes. A solution of sodium dithionite (16.50 g, 94.8 mmol) in water (51 mL) was added, and the mixture was stirred for 10 minutes. Further, a solution of sodium dithionite (11.10 g, 63.8 mmol) in water (51 mL) was added, followed by stirring for 10 minutes. A 4 mol/L aqueous solution of sulfuric acid (201 mL) was added, and the mixture was stirred at 90° C. for 30 minutes. After allowing the reaction mixture to cool down to room temperature, 28% aqueous ammonia (310 mL) was added to the reaction mixture in an ice bath, followed by stirring for 30 minutes. The mixture was extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was recrystallized from hexane to obtain the title compound (32.91 g, 80%) as pale yellow needles.

1. stirringby stirring for 15 minutes
2. stirringthe mixture was stirred for 10 minutes
3. stirringby stirring for 10 minutes
4. stirringthe mixture was stirred at 90° C. for 30 minutes
5. temperatureto cool down to room temperature
6. stirringby stirring for 30 minutes
7. extractionThe mixture was extracted with chloroform
8. washThe organic layer was washed with brine
9. dry with materialdried over anhydrous sodium sulfate
10. concentrationconcentrated under reduced pressure
11. customThe residue was recrystallized from hexane

ORD record

ord-9e1f3f3001b442e6b7d67c957ff59019

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07750150B2