1: 68 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) 25 deg C, 12 h 2: 95 percent / trifluoroacetic anhydride, trifluoroacetic acid / 18 h / Ambient temperature 3: 93 percent / dimethylformamide / 18 h / Ambient temperature 4: 1.) hydrogen, 2.) HCl / 1.) 20percent Pd/C / 1.) glacial AcOH, 50 psi, 18 h, 2.) EtOH, 2-propanol 5: 1.) BBr3, 2.) HCl / 1.) 1,2-dichloroethane, reflux, 1.5 h, 2.) 2-propanol, 25 deg C, 2 h 6: 2.) aq. NH4OH / 1.) EtOH, reflux, 7 d 7: methylhydrazine / methanol / 25 °C View Scheme

1: oxaloyl chloride / toluene; dimethylformamide / 0.5 h / 70 °C 2: 84 percent / K2CO3 / H2O; toluene / 11 h / 0 °C 3: 58 percent / BH3*SMe2 / tetrahydrofuran / 12 h / Heating 4: 93 percent / K2CO3 / dimethylformamide / 4 h / 135 °C / other dihalo-3-nitrobenzyl diamines, regioselectivity 5: 65 percent / K2CO3 / dimethylformamide / 24 h / 23 °C 6: H2 / 5percent Pd/C / methanol / 0.33 h / 23 °C 7: methanol / 6.5 h View Scheme

tris-(2-chloro-ethyl)-amine; sulfuric acid

T=75°C; 24 h;

1: 68 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) 25 deg C, 12 h 2: 95 percent / trifluoroacetic anhydride, trifluoroacetic acid / 18 h / Ambient temperature 3: 93 percent / dimethylformamide / 18 h / Ambient temperature 4: 1.) hydrogen, 2.) HCl / 1.) 20percent Pd/C / 1.) glacial AcOH, 50 psi, 18 h, 2.) EtOH, 2-propanol 5: BBr3 / 1,2-dichloro-ethane / 1.5 h / Heating View Scheme

1: 83 percent / N,N-dimethylaniline / 18 h / Heating 2: 88 percent / N,N-dimethylaniline, POCl3 / 1,2-dichloro-ethane / 18 h / Heating 3: 70 percent / tetrahydrofuran; methanol / 18 h / Ambient temperature View Scheme

1: 83 percent / N,N-dimethylaniline / 18 h / Heating 2: 88 percent / N,N-dimethylaniline, POCl3 / 1,2-dichloro-ethane / 18 h / Heating 3: 89 percent / tetrahydrofuran; methanol / 7.5 h / Ambient temperature View Scheme

1: 47 percent / N,N-dimethylaniline, N,N-diisopropylethylamine / 18 h / Heating 2: N,N-dimethylaniline, POCl3 / 1,2-dichloro-ethane / 0.5 h / Heating 3: 98 percent / BBr3 / CH2Cl2; 1,2-dichloro-ethane / 2 h / Heating 4: 72 percent / tetrahydrofuran; methanol / 88 h / 60 °C 5: 70 percent / N,N-diisopropylethylamine / 1,2-dichloro-ethane / 1.5 h / 60 °C View Scheme

1: 47 percent / N,N-dimethylaniline, N,N-diisopropylethylamine / 18 h / Heating 2: 62 percent / N,N-dimethylaniline, POCl3 / CHCl3 / 1.5 h / Heating 3: 84 percent / methanesulfonic acid / acetic acid / 8 h / Heating View Scheme

T=125 - 130°C; 0.333333 h;