in isobutyramide T=165°C; 5 h;

in diethylene glycol dimethyl ether T=130 - 140°C; 3 h;

in N,N-dimethyl acetamide T=140 - 142°C; 8 h;

1: 71 percent / hydrochloric acid, iron / methanol; dioxane / 0.5 h / Heating 2: 1.) sodium nitrite, sulfuric acid, 2.) potassium iodide, aq. sulfuric acid / 1.) acetic acid, 40 deg C, 30 min, 2.) RT, 60 min 3: 90 percent / iron, concentrated hydrochloric acid / methanol / 0.17 h 4: 46 percent / bis-(2-methoxy-ethyl) ether / 3 h / 130 - 140 °C View Scheme

1: 1.) sodium nitrite, sulfuric acid, 2.) potassium iodide, aq. sulfuric acid / 1.) acetic acid, 40 deg C, 30 min, 2.) RT, 60 min 2: 90 percent / iron, concentrated hydrochloric acid / methanol / 0.17 h 3: 46 percent / bis-(2-methoxy-ethyl) ether / 3 h / 130 - 140 °C View Scheme

1: 90 percent / iron, concentrated hydrochloric acid / methanol / 0.17 h 2: 46 percent / bis-(2-methoxy-ethyl) ether / 3 h / 130 - 140 °C View Scheme

1: 82 percent / dimethylformamide / 2 h / 140 - 150 °C 2: 71 percent / hydrochloric acid, iron / methanol; dioxane / 0.5 h / Heating 3: 1.) sodium nitrite, sulfuric acid, 2.) potassium iodide, aq. sulfuric acid / 1.) acetic acid, 40 deg C, 30 min, 2.) RT, 60 min 4: 90 percent / iron, concentrated hydrochloric acid / methanol / 0.17 h 5: 46 percent / bis-(2-methoxy-ethyl) ether / 3 h / 130 - 140 °C View Scheme

1: 90 percent / NH3(g) / dimethylsulfoxide / 24 h / 75 - 90 °C 2: 1.)NaNO2/aq. HCl 2.)KI / 1.)0 to -5 deg C, 1 h 2.)r.t., 15 h 3: 74 percent / N,N-dimethyl-acetamide / 8 h / 140 - 142 °C View Scheme

1: 1.)NaNO2/aq. HCl 2.)KI / 1.)0 to -5 deg C, 1 h 2.)r.t., 15 h 2: 74 percent / N,N-dimethyl-acetamide / 8 h / 140 - 142 °C View Scheme