acetic acid; sodium nitrite in water T=0 - 20°C; 3.5 h;

1: 20 percent Turnov. / 15-crown-5; NaNH2 / xylene / 1.5 h / 130 °C 2: 52 percent Turnov. / NaNO2; acetic acid / H2O / 3.5 h / 0 - 20 °C View Scheme

hydrazine hydrate; palladium on activated charcoal in tetrahydrofuran T=-20 - 0°C; 1.5 h;