ammonia in methanol T=175°C; 6 h;

Raney nickel W-5 in ethanol; 2-methoxy-ethanol; water T=120°C; 1 h;

sodium in 2-methoxy-ethanol

ammonia in ethanol T=120°C; 8 h;

sodium methylate in dimethyl sulfoxide 4 h; Ambient temperature;

1: GNO3 With sodium methylate T=30°C; 0.5 h; Reflux; 2: 3-anilino-2-(3,4,5-trimethoxybenzyl)propenenitrile 10 h; Reflux;

1: NaOMe / dimethylsulfoxide 2: DMSO / ethanol View Scheme

in ethanol; dimethyl sulfoxide 18 h; Heating;

1.1: i-PrMgCl*LiCl / tetrahydrofuran; 1,2-dimethoxy-ethane / 4 h / 0 °C 1.2: CuBr; P(OEt)3 / 1,2-dimethoxy-ethane; tetrahydrofuran / 0.17 h / -15 °C 1.3: 81 percent / tetrabutylammonium iodide / tetrahydrofuran; 1,2-dimethoxy-ethane / 1.5 h / 60 °C 2.1: 87 percent / aq. HCl / methanol / 0.25 h / 20 °C 3.1: 86 percent / N,N-dimethylbenzenamine; POCl3 / 1 h / 110 °C 4.1: 85 percent / NH3 / methanol / 6 h / 175 °C View Scheme

1: 86 percent / N,N-dimethylbenzenamine; POCl3 / 1 h / 110 °C 2: 85 percent / NH3 / methanol / 6 h / 175 °C View Scheme