Cl.O.[Cl-].[NH4+].[Cl:5][C:6]1[C:11]([CH3:12])=[C:10]([NH:13]O)[C:9]([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([F:22])[CH:16]=2)=[C:8]([C:23](=[O:25])[CH3:24])[CH:7]=1>C(O)C.[Fe]>[NH2:13][C:10]1[C:9]([C:15]2[CH:16]=[C:17]([F:22])[CH:18]=[C:19]([F:21])[CH:20]=2)=[C:8]([C:23](=[O:25])[CH3:24])[CH:7]=[C:6]([Cl:5])[C:11]=1[CH3:12]
Into a flask was placed a suspension of iron (1.50 g, 26.9 mmol) (<10 μm) in ethanol (22 mL) δ 0 M hydrogen chloride in water (0.374 mL, 2.24 mmol) was added and the suspension was stirred for 2 h at 60° C. A solution of 5.0 M ammonium chloride in water (3.86 mL, 19.3 mmol) was added followed by a solution of 1-[4-chloro-3′,5′-difluoro-6-(hydroxyamino)-5-methylbiphenyl-2-yl]ethanone (1.4 g, 4.5 mmol) in ethanol (5.2 mL). The resulting suspension was stirred at 60° C. for 1 hour. The mixture was cooled, filtered and evaporated in vacuo. The residue was dissolved in a mixture of ethyl acetate and saturated sodium bicarbonate solution and stirred for a few minutes. The layers were separated and the ethyl acetate layer was washed with brine, dried over MgSO4 and evaporated in vacuo to give the desired product (0.95 g, 72%). LCMS calculated for C15H13ClF2NO (M+H)+: m/z=296.1. found: 296.0.
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