Ammonium Chloride → 3',4'-Diamino-3-fluoro-[1,1'-biphenyl]-4-carbonitrile

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Reaction Steps

To a warm solution of 4′-amino-3-fluoro-3′-nitro-[1,1′-biphenyl]-4-carbonitrile (Preparation 85, 0.86 g, 3.3 mmol) in ethanol (75 mL) was added saturated aqueous ammonium chloride solution (12 mL, 180 mmol) and iron (2.41 g, 43.2 mmol). The reaction solution was heated to reflux for 1 hour. The reaction mixture was allowed to cool, filtered, and the filtrate was adjusted to pH=9 with saturated aqueous sodium hydrogen carbonate solution and then the mixture was concentrated in vacuo to a residue. The residue was treated with methanol and the resulting suspension was filtered and the filtrate concentrated to dryness. The residue was purified using silica gel column chromatography eluting with 0-10% MeOH in DCM to afford the title compound (0.34 g, 45%) as a yellow solid.

Provenance & Evidence