1: (E,Z)-crotononitrile With hydrazine in tetrahydrofuran; water T=0 - 20°C; 2.33 h; 2: 4-methoxy-benzaldehyde in tetrahydrofuran; water T=20°C; 3.25 h; 3: With sodium n-butanolate in butan-1-ol T=25 - 120°C; 3.33 h;

1: methyl acetate; acetonitrile With potassium tert-butylate in tetrahydrofuran T=5 - 20°C; 2: (4-methoxybenzyl)hydrazine dihydrochloride in tetrahydrofuran 0.0833333 h;

hydrogenchloride in 1,4-dioxane Reflux;

1: ethanol / Reflux 2: 10 palladium on activated charcoal; hydrogen / ethanol / 10 - 20 °C / 775.74 Torr 3: hydrogenchloride / methanol / 40 - 60 °C 4: hydrogenchloride / 1,4-dioxane / Reflux View Scheme