2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in benzene 7.5 h; Inert atmosphereReflux;

1: With hydrogenchloride in ethanol; water 6 h; Reflux; 2: With sodium hydrogencarbonate in ethanol; water 72 h; Reflux;

in tetrahydrofuran T=20°C; 2 h;

in benzene 16 h; Heating;

1: 89 percent / pyridine / CH2Cl2 / 15 h / Heating 2: 5 percent / 1-methyl-1-phenylhydrazine / bis-(2-methoxy-ethyl) ether / 4.5 h / Heating View Scheme

1: thionyl chloride / CH2Cl2 2: 89 percent / pyridine / CH2Cl2 / 15 h / Heating 3: 5 percent / 1-methyl-1-phenylhydrazine / bis-(2-methoxy-ethyl) ether / 4.5 h / Heating View Scheme

N1-methyl-N1-phenyl hydrazine in diethylene glycol dimethyl ether 4.5 h; Heating;

in tetrahydrofuran T=20°C; 3 h;

1.1: sodium t-butanolate / 0.5 h / 35 °C / Molecular sieve; Cooling with ice 1.2: 12 h / 50 °C / Cooling with ice 2.1: sodium hydrogencarbonate / methanol / 0.5 h / 20 °C 2.2: 6 h / 50 °C 3.1: hydrogenchloride; iron / methanol; water / 3 h / Reflux 4.1: potassium carbonate / methanol; water / 6 h / Reflux 5.1: hydrogenchloride / ethanol; water / 6 h / Reflux 5.2: 72 h / Reflux View Scheme

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