Sulfuric Acid → 3'-Hydroxybiphenyl-2-carbonitrile

HRID 895141Notes

Reaction equation

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]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A 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), brine (300 ml) and dried (Na2SO4). Filtration and concentration 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).

Workup

temperatureOn cooling to ambient temperature the product
extractionwas extracted into ethyl acetate (500 ml)
washthe organic layer was washed with water (300 ml), brine (300 ml)
dry with materialdried (Na2SO4)
filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record: ord-7a0962f8b5584c93b96de7ea8a678997
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06914065B2

Reaction notes

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