1: 88 percent / pyridine / 48 h / Ambient temperature 2: phosphoryl chloride, N,N-diethylaniline / 0.08 h / Heating 3: 45 percent / ammonia gas / methanol / 15 h / 100 °C 4: 18 percent / Raney nickel / H2O / 3 h / Heating View Scheme

sodium hydroxide; water; nickel-aluminum alloy T=60°C; pH=14.3; 4 - 15 h; Product distribution / selectivity;

1: 60 percent / NEt3 / dimethylformamide / 2 h / 40 °C 2: 91 percent / perfluorobutanesulfonyl fluoride; i-Pr2NEt / ethyl acetate / 20 h / 65 °C 3: 61 percent / Raney Ni / toluene / 14 h / 90 °C 4: 69 percent / aq. AcOH / 2 h / 80 °C View Scheme