[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][C:9]=1[N+:16]([O-])=O)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C>CO.C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][C:9]=1[NH2:16])([CH3:4])([CH3:2])[CH3:3]To solution of (4-cyano-2-nitrophenyl)-carbamic acid tert-butyl ester (3.6 g, 13.8 mmol) in methanol (18 mL), ethyl acetate (28 mL) and triethylamine (1.9 mL, 13.6 mmol) was added 10% Pd on carbon (0.73 g, 0.69 mmol). The reaction mixture was hydrogenated under 1 atm H2 for 24 hours, filtered through Celite and concentrated in vacuo. The residue was purified by flash chromatography in silica gel using 20% ethyl acetate in n-heptane as eluent to afford (2-amino-4-cyanophenyl)-carbamic acid tert-butyl ester (2.6 g, 82%) as a light yellow solid.
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