methylhydrazine in tetrahydrofuran T=0 - 20°C; dephthaloylation;

sodium hydroxide in dichloromethane T=0 - 20°C;

1: 79 percent / NH2NH2; H2 / 10percent Pd/C / methanol / 20 °C 2: 38 percent / 1 M NaOH / CH2Cl2 / 0 - 20 °C View Scheme

1: H2 / Pd-C / tetrahydrofuran 2: aq. NaOH / CHCl3 3: aq. HCl / ethyl acetate View Scheme

1: tetrahydrofuran / 0.08 h / 20 °C 2: 1,3-dicyclohexylcarbodiimide / tetrahydrofuran / 1 h 3: acetic acid; triethylamine / tetrahydrofuran / 1 h / Heating 4: 84 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 0.5 h / 0 - 5 °C 5: 90 percent / methylhydrazine / tetrahydrofuran / 0 - 20 °C View Scheme

hydrogenchloride in ethyl acetate

1: aq. NaOH / CHCl3 2: aq. HCl / ethyl acetate View Scheme

Multistep reaction;