hydrogen; palladium on activated charcoal in acetone

1: 1.) triethylamine; 2.) 60 percent KOH / 1.) 175 deg C, 1 h; 2.) methanol, 30 min, reflux 2: 20 percent / KOH, K2S2O8 / H2O / 12 h 3: 62 percent / K2CO3 / acetone / 1 h / Heating 4: 75 percent / H2 / Pd/C / acetone View Scheme

1: 66.6 percent / K2CO3 / dimethylformamide / 1 h / Heating 2: 84 percent / silver nitrate, 40 percent NaOH / H2O / 0.5 h / Heating 3: 73 percent / pyridine, thionyl chloride / benzene / 14 h 4: 1.) triethylamine; 2.) 60 percent KOH / 1.) 175 deg C, 1 h; 2.) methanol, 30 min, reflux 5: 20 percent / KOH, K2S2O8 / H2O / 12 h 6: 62 percent / K2CO3 / acetone / 1 h / Heating 7: 75 percent / H2 / Pd/C / acetone View Scheme