sulfuric acid; nitric acid; acetic anhydride 2.) reflux, 12 h; Yield given. Multistep reaction. Yields of byproduct given;

1: 1-methyl-pyrrole; 2,2,2-trichloroacetyl chloride 2: With nitric acid 3: sodium methylate

1: aq. NaOH / tetrahydrofuran; methanol 2: thionyl chloride / 2 h / 60 °C View Scheme

1: N-Methyl-4-nitropyrrole-2-carboxylic Acid Methyl Ester With hydrogen; palladium 10 on activated carbon in ethyl acetate T=20°C; 12 h; 2: di-tert-butyl dicarbonate in diethyl ether T=20°C; 2 h; 3: With sodium hydroxide in methanol; water T=60°C; 2 h;

1: H2 / Ni-raney / ethanol / 12 h / 50 °C 2: 84 percent / CH2Cl2 / 12 h / Heating 3: 93 percent / aq. NaOH / methanol / 18 h / Heating View Scheme

View Scheme

1: 92 percent / aq. NaOH / Heating 2: SOCl2 / tetrahydrofuran / 0.08 h / Heating 3: Hunig's base / tetrahydrofuran / -20 - 20 °C 4: 1.) H2, 2.) HCl / 10percent Pd/C / 1.) methanol, 40 deg C, 1 atm, 2.) isopropanol, -30 deg C 5: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature 6: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT 7: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C 8: methanol; tetrahydrofuran / 0.5 h / -40 °C View Scheme

1: 92 percent / aq. NaOH / Heating 2: SOCl2 / tetrahydrofuran / 0.08 h / Heating 3: Hunig's base / tetrahydrofuran / -20 - 20 °C View Scheme

1: H2 / Ni-raney / ethanol / 12 h / 50 °C 2: 84 percent / CH2Cl2 / 12 h / Heating View Scheme

alkaline solution