3-AMINO-4-FLUOROBENZONITRILE

General procedure: Before each run, the system (see Fig.4) was allowed to equilibrate by pumping solvent through for 30min with the Tube-in-Tube device at 16bar of hydrogen. An omnifit cartridge (20.0mm OD, 15.0mm ID) containing 1g of Pd-C catalyst was used. To avoid an overpressure of the system in the event of blockage, the upper pressure cut-off limit on the Knauer pump was set to 25bar. With the injection loop disconnected from the flow line, the loop was opened and filled manually (using a syringe) with 3.6mL of a 0.076M solution of starting material in ethanol (excess starting material solution exiting the loop was recovered for reuse). The injection loop was then closed off and switched into the flow stream. The outlet from the system (downstream of the back-pressure regulator) was collected for 120min. The solvent was removed under reduced pressure (using a rotary evaporator followed by a 2-stage rotary vane pump) to afford the product.Intermediate 1: 3-Amino-4-fluoro benzonitrile; A solution of 4-fluoro-3-nitro benzonitrile (Combi-Blocks; 5.0 g; 30 mmol) and saturated solution of ammonium chloride (16 g; 0.3 mol in 20ml of water) in iPrOH (100 ml) was treated with iron powder (8.4 g; 0.15 mol) and refluxed for 4h. The mixture was cooled and diluted with ethyl acetate (200ml) and the organic phase was washed with water, brine and dried on MgSO^ The solvents were evaporated under reduced pressure and the residue was purified by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc to give the Title compound (3.5 g, 87percent) as a solid.

Molecular Weight:136.13
XLogP3:1.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:136.04367633
Monoisotopic Mass:136.04367633
Topological Polar Surface Area:49.8
Heavy Atom Count:10
Complexity:160
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes