N[C:2]1[CH:3]=[C:4]([C:8]2[C:9]([C:14]#[N:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)[OH:17].N([O-])=O.[Na+]>O1CCOCC1.O>[OH:17][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([C:14]#[N:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1A solution of 3′-aminobiphenyl-2-carbonitrile (10.9 g, 56 mmol) in 1,4-dioxane (30 ml) was treated with a solution of 25% aqueous sulfuric acid (150 ml). The resulting suspension was cooled to 0° C. before being treated dropwise over 10 minutes with a solution of sodium nitrite (4.6 g, 67 mmol) in water (10 ml). After stirring at 0° C. for 30 minutes the reaction was poured into hot (70° C.) water (500 ml). On cooling to ambient temperature the product was extracted into ethyl acetate (500 ml), the organic layer was washed with water (300 ml), then brine (300 ml) and dried (Na2SO4). Filtration and evaporation in vacuo afforded 7.1 g (65%) of 3′-hydroxybiphenyl-2-carbonitrile as a dark oil: 1H NMR (400 MHz, CDCl3) δ 5.40 (1H, br), 6.92 (1H, ddd, J 8, 3, 1 Hz), 7.04 (1H, dd, J 3, 3 Hz), 7.11 (1H, ddd, J 8, 3, 1 Hz), 7.35 (1H, dd, J 8, 8 Hz), 7.44 (1H, ddd, J 8, 8, 1 Hz), 7.51 (1H, dd, J 8, 1 Hz), 7.64 (1H, ddd, J 8, 8, 1 Hz), 7.75 (1H, dd, J 8, 1 Hz).
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