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

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.

1. temperatureThe reaction solution was heated
2. temperatureto reflux for 1 hour
3. temperatureto cool
4. filtrationfiltered
5. concentrationthe mixture was concentrated in vacuo to a residue
6. additionThe residue was treated with methanol
7. filtrationthe resulting suspension was filtered
8. concentrationthe filtrate concentrated to dryness
9. customThe residue was purified
10. washeluting with 0-10% MeOH in DCM

ORD record

ord-5193f86a454149478bc12c45702d8318

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08927587B2