[C:1]([C:5]1[CH:6]=[C:7]([N+:18]([O-])=O)[C:8]([O:16][CH3:17])=[C:9]([C:11]([CH3:15])([CH3:14])[C:12]#[N:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+].O>C(O)C.[Fe]>[NH2:18][C:7]1[C:8]([O:16][CH3:17])=[C:9]([C:11]([CH3:15])([CH3:14])[C:12]#[N:13])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=1
To a solution of 2-(5-tert-butyl-2-methoxy-3-nitrophenyl)-2-methylpropanenitrile (0.086 g, 0.311 mmol) in ethanol (3.1 mL), iron (0.087 g, 1.56 mmol), ammonium chloride (0.083 g, 1.56 mmol) and water (1.6 mL) were added, and the mixture was stirred for 3 hours under reflux. The reaction mixture was filtered and washed with ethanol. The obtained filtrate was evaporated under reduced pressure and the residue was dissolved in dichloromethane. After washing this solution with water and then saturated brine, the solution was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=0/100-30/70) to obtain 0.051 g of the captioned compound (67% yield).
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