1: 1.) thionyl chloride, water / 1.) reflux, 4 d; other reagents: SOCl2/H2O/HCl, SOCl2/H2O/H2SO4, SOCl2/H2O/H2SO3, 2.) toluene 2: hydrazine hydrate / methanol / 2 h View Scheme

methanol; hydrazine hydrate

2: methanol; N2H4+H2O View Scheme

1: With potassium tert-butylate in tetrahydrofuran; N,N-dimethyl-formamide T=20°C; 2 h; Inert atmosphere; 2: 4-chloropicolinohydrazide With potassium carbonate in tetrahydrofuran; N,N-dimethyl-formamide T=80°C; 6 h; Inert atmosphere;

hydrogenchloride; acetic acid; sodium nitrite 1.) water, 15 min, 2.) water, heating; Yield given. Multistep reaction;

toluene-4-sulfonic acid T=130°C; 0.583333 h;