[C:1]([O:5][C:6](=[O:18])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]#[N:17])([CH3:4])([CH3:3])[CH3:2].[OH-].[NH4+].[H][H]>[Ni].CO>[C:1]([O:5][C:6](=[O:18])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[CH2:16][NH2:17])([CH3:4])([CH3:2])[CH3:3]Raney nickel (˜0.5 g) was added to a solution of 2-cyano-4-chlorophenoxy acetic acid-t-butyl ester (560 mg, 0.21 mmol) in methanol (25 mL) containing 1 mL of sat. ammonium hydroxide. The mixture was placed under 40 psi of hydrogen and shaken for two hours. The mixture was filtered and concentrated. The residue was partitioned between 1 N HCl and ether. The layers were separated and the aqueous layer was re-extracted with ether. The aqueous layer was basified to ˜pH with K2CO3 solution and extracted with ether (3×). The combined organic layers were dried (MgSO4), filtered and concentrated to afford 360 mg of the title compound as an oil. MS 272 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 7.22 (s, 1H); 7.12 (d, 1H, J=8.7 Hz); 6.61 (d, 1H, J=8.7 Hz); 4.5 (s, 2H); 3.85 (s, 2H); 2.62 (bs, 2H); 1.41 (s, 9H).
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