ammonia in methanol T=175°C; 6 h;

ammonia in ethanol T=120°C; 8 h;

N,N-dimethyl-aniline; trichlorophosphate T=110°C; 1 h;

triethylsilane in trifluoroacetic acid Ambient temperature;

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 View Scheme

1: 87 percent / aq. HCl / methanol / 0.25 h / 20 °C 2: 86 percent / N,N-dimethylbenzenamine; POCl3 / 1 h / 110 °C View Scheme

1.1: 83 percent / DMAP; Et3N / tetrahydrofuran / 4 h / 20 °C 2.1: i-PrMgCl*LiCl / tetrahydrofuran; 1,2-dimethoxy-ethane / 4 h / 0 °C 2.2: CuBr; P(OEt)3 / 1,2-dimethoxy-ethane; tetrahydrofuran / 0.17 h / -15 °C 2.3: 81 percent / tetrabutylammonium iodide / tetrahydrofuran; 1,2-dimethoxy-ethane / 1.5 h / 60 °C 3.1: 87 percent / aq. HCl / methanol / 0.25 h / 20 °C 4.1: 86 percent / N,N-dimethylbenzenamine; POCl3 / 1 h / 110 °C View Scheme

1: 1) lithium diisopropylamide / 1) THF, -78 deg C, 1 h, 2) -78 deg C, 1 h 2: 79 percent / triethylsilane / trifluoroacetic acid / Ambient temperature View Scheme