Ammonia → 2-Amino-3-fluorobenzonitrile

Temperature

140 °C

A mixture of 2,3-difluorobenzonitrile (19.0 g, 137 mmol) and ethanol (200 ml) pre-saturated with ammonia gas was heated at 140° C. in an autoclave for 8 h (terminal pressure 200 psi). The mixture was allowed to cool to ambient temperature and evaporated to dryness. The residue was dissolved in water (400 ml) and extracted with diethyl ether (2×300 ml). The combined organics were washed with water (300 ml) and brine (250 ml), dried over anhydrous magnesium sulfate, filtered and evaporated. Trituration with isohexane (150 ml) afforded 2-amino-3-fluorobenzonitrile (9.8 g, 50%) as an off-white solid: 1H NMR (360 MHz, CDCl3) δ 4.47 (2H, s), 6.65-6.71 (1H, m), 7.14-7.20 (2H, m).

1. temperatureto cool to ambient temperature
2. customevaporated to dryness
3. dissolutionThe residue was dissolved in water (400 ml)
4. extractionextracted with diethyl ether (2×300 ml)
5. washThe combined organics were washed with water (300 ml) and brine (250 ml)
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered
8. customevaporated

ORD record

ord-9c0f70289db243e283c1d396b89f1fe9

Source dataset

uspto-grants-2005_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06936608B2