1: 86.2 percent / 50percent NaH / dimethylformamide; benzene / 1.) room temp., 15 min; 2.) room temp., 10 h 2: 77.6 percent / TiCl3 / tetrahydrofuran / 0.33 h / Ambient temperature 3: 1.) NaNO2/2 N HCl, 2.) aq. NaBF4 / 1.) H2O/THF, room temp., 20 min; 2.) H2O/THF, room temp., 30 min 4: 40.2 percent / 0.08 h / 187 °C 5: 53.6 percent / 40percent aq. NaOH / methanol / 2 h / Heating View Scheme

1: 86.2 percent / 50percent NaH / dimethylformamide; benzene / 1.) room temp., 15 min; 2.) room temp., 10 h 2: 77.6 percent / TiCl3 / tetrahydrofuran / 0.33 h / Ambient temperature 3: NaNO2/2 N HCl 4: CuCl/concd. HCl / 1.) room temp., 0.5 h; 2.) 95 deg C, 5 min 5: 78.1 percent / 40percent aq. NaOH / methanol / 2 h / Heating View Scheme

1: 86.2 percent / 50percent NaH / dimethylformamide; benzene / 1.) room temp., 15 min; 2.) room temp., 10 h 2: 77.6 percent / TiCl3 / tetrahydrofuran / 0.33 h / Ambient temperature 3: NaNO2/4.7percent aq. HBr 4: CuBr/concd. HBr / 1.) room temp., 20 min; 2.) 95 deg C, 5 min 5: 93.9 percent / 40percent aq. NaOH / methanol / 2 h / Heating View Scheme

in water; N,N-dimethyl-formamide 1 h; Heating / reflux;

sodium tetrahydroborate in methanol; formamide T=100°C; 5 h;

in water; N,N-dimethyl-formamide 1 h; Reflux;

1: 82.5 percent / H2O; aq. acetic acid / 12 h / Ambient temperature 2: 55.9 percent / H2O; dimethylformamide / 1.5 h / Heating View Scheme

in water; N,N-dimethyl-formamide 1.5 h; Heating;

sodium tetrahydroborate; sodium cyanide 1.) 18 deg C, 1 h, 2.) reflux, 5 h; Yield given. Multistep reaction. Yields of byproduct given;

1: H2 / 10percent Pd/C / 3800 Torr 2: pyridine 3: 1.) NaH 4: 100 percent / aq. NaOH 5: pyridine 6: 77 percent / Fremy's salt 7: 41 percent / benzylamine hydrochloride, NaHCO3 / acetonitrile; methanol View Scheme