Ammonia → 3,5-Difluorobenzylamine

A slurry of Raney nickel in methanol was added to a solution of 3,5-difluorobenzonitrile (12.0 g, 0.0863 mole) in methanol (100 ml) saturated with ammonia and th emixture was hydrogenated for 2.5 hours at 50 pounds pressure. The solution was decanted from the catalyst and the catalyst washed four times with methanol and decanted. The combined decanted solvent was evaporated and the residue dissolved in ethyl acetate and extracted twice with 1N hydrochloric acid (50 ml). The acid solution was made basic with 10% sodium hydroxide and extracted with three portions of ethyl acetate. The ethyl acetate was washed with water, brine, dried over sodium sulfate and the solvent removed to give 3,5-difluorobenzylamine as an oil (12.3 g, 100%).

1. customThe solution was decanted from the catalyst
2. washthe catalyst washed four times with methanol
3. customdecanted
4. customThe combined decanted solvent
5. customwas evaporated
6. dissolutionthe residue dissolved in ethyl acetate
7. extractionextracted twice with 1N hydrochloric acid (50 ml)
8. extractionextracted with three portions of ethyl acetate
9. washThe ethyl acetate was washed with water, brine
10. dry with materialdried over sodium sulfate
11. customthe solvent removed

ORD record

ord-949c70c75ffc4fc4be04810a0698200c

Source dataset

uspto-grants-1989_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04837353