hydrogen; palladium on activated charcoal in ethyl acetate T=25°C; P=735.5 Torr;

1.1: 77 percent / H2SO4 / CH2Cl2 / Heating 2.1: 67 percent / pyridine / CH2Cl2 / 48 h / 20 °C 3.1: K2CO3 / dimethylformamide 3.2: 70 percent / dimethylformamide / 1.5 h / 35 °C 4.1: 50 percent / K2CO3 / methanol / 3 h / 20 °C View Scheme

1: aqueous NaOH 2: sodium methylate View Scheme

hydrogenchloride