methylhydrazine in methanol T=25°C;

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: 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: 93 percent / dimethylformamide / 18 h / Ambient temperature 2: 1.) hydrogen, 2.) HCl / 1.) 20percent Pd/C / 1.) glacial AcOH, 50 psi, 18 h, 2.) EtOH, 2-propanol 3: 1.) BBr3, 2.) HCl / 1.) 1,2-dichloroethane, reflux, 1.5 h, 2.) 2-propanol, 25 deg C, 2 h 4: 2.) aq. NH4OH / 1.) EtOH, reflux, 7 d 5: methylhydrazine / methanol / 25 °C View Scheme

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