1: SOCl2 / dimethylformamide / Heating 2: (i-Pr)2NEt / tetrahydrofuran / 48 h / 25 °C 3: 2N aq. NaOH / 10 h / Heating 4: NaH / dimethylformamide / Ambient temperature 5: 88 percent / H2 / 10percent Pd/C / ethanol / 16 h / 2585.7 Torr 6: 1.) 35percent aq. H2SO4, NaNO2, 2.) Cu(NO3)2*2.5H2O, CuO / 1.) 0 deg C, 30 min, 2.) water, 15 min View Scheme

1: (i-Pr)2NEt / tetrahydrofuran / 48 h / 25 °C 2: 2N aq. NaOH / 10 h / Heating 3: NaH / dimethylformamide / Ambient temperature 4: 88 percent / H2 / 10percent Pd/C / ethanol / 16 h / 2585.7 Torr 5: 1.) 35percent aq. H2SO4, NaNO2, 2.) Cu(NO3)2*2.5H2O, CuO / 1.) 0 deg C, 30 min, 2.) water, 15 min View Scheme

sulfuric acid; copper(II) nitrate; copper(II) oxide; sodium nitrite 1.) 0 deg C, 30 min, 2.) water, 15 min; Yield given. Multistep reaction;