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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence