Stannous chloride dihydrate → 5'-Amino-5,2'-difluorobiphenyl-2-carbonitrile

5,2′-Difluoro-5′-nitrobiphenyl-2-carbonitrile (3.25 g, 12.5 mmol) in tetrahydrofuran (20 ml) and ethanol (20 ml) was treated with tin(II) chloride dihydrate (9.86 g, 43.8 mmol) and the mixture left to stir at ambient temperature for 18 h. The solvent was evaporated and the residue stirred with 2 N sodium hydroxide solution (40 ml) for 2 h. The resulting suspension was diluted with water (100 ml) and extracted with dichloromethane (3×200 ml). The combined organics were washed with water (200 ml), brine (200 ml), dried over anhydrous sodium sulfate, filtered and evaporated to give the title compound as a brown solid: 1H NMR (360 MHz, CDCl3) δ 3.68 (2H, s), 6.67-6.76 (2H, m), 7.02 (1H, dd, J 9, 9 Hz), 7.12-7.27 (2H, m), 7.78 (1H, dd, J 9, 6 Hz).

1. waitthe mixture left
2. customThe solvent was evaporated
3. stirringthe residue stirred with 2 N sodium hydroxide solution (40 ml) for 2 h
4. additionThe resulting suspension was diluted with water (100 ml)
5. extractionextracted with dichloromethane (3×200 ml)
6. washThe combined organics were washed with water (200 ml), brine (200 ml)
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationfiltered
9. customevaporated

ORD record

ord-483ad14db0684769af553791cde0986a

Source dataset

uspto-grants-2005_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06936608B2