iron; ammonium chloride in toluene T=85 - 90°C; 1 h;

1: 86 percent / HNO3, conc. H2SO4 / 1 h / 0 - 5 °C 2: 79 percent / 0.78N aq. NH4Cl, Fe / toluene / 1 h / 85 - 90 °C View Scheme

1: aq. NaHCO3 / CHCl3 / 2 h / 0 - 10 °C 2: K2CO3 / dimethylformamide / 2 h / 70 °C 3: 82.2 percent / K2CO3 / dimethylformamide / a) RT, 3 h, b) 40-45 deg C, 1 h 4: 81.5 percent / 5percent NaOH / ethanol / 3 h / Heating 5: 97.5 percent / NaOH, H2 / Pd/C / H2O; ethanol / 5.5 h View Scheme

1: aq. NaHCO3 / CHCl3 / 2 h / 0 - 10 °C 2: K2CO3 / dimethylformamide / 2 h / 70 °C 3: 82.2 percent / K2CO3 / dimethylformamide / a) RT, 3 h, b) 40-45 deg C, 1 h View Scheme

1: aq. NaHCO3 / CHCl3 / 2 h / 0 - 10 °C 2: K2CO3 / dimethylformamide / 2 h / 70 °C 3: 82.2 percent / K2CO3 / dimethylformamide / a) RT, 3 h, b) 40-45 deg C, 1 h 4: 81.5 percent / 5percent NaOH / ethanol / 3 h / Heating View Scheme

1: aq. NaHCO3 / CHCl3 / 2 h / 0 - 10 °C 2: K2CO3 / dimethylformamide / 2 h / 70 °C 3: 82.2 percent / K2CO3 / dimethylformamide / a) RT, 3 h, b) 40-45 deg C, 1 h 4: 81.5 percent / 5percent NaOH / ethanol / 3 h / Heating 5: SOCl2, DMF / 1,2-dichloro-ethane / 2 h / 60 °C 6: CHCl3 / 1 h / Ambient temperature View Scheme

1: aq. NaHCO3 / CHCl3 / 2 h / 0 - 10 °C 2: K2CO3 / dimethylformamide / 2 h / 70 °C View Scheme

1: aq. NaHCO3 / CHCl3 / 2 h / 0 - 10 °C 2: K2CO3 / dimethylformamide / 2 h / 70 °C 3: 82.2 percent / K2CO3 / dimethylformamide / a) RT, 3 h, b) 40-45 deg C, 1 h 4: 81.5 percent / 5percent NaOH / ethanol / 3 h / Heating 5: SOCl2, DMF / 1,2-dichloro-ethane / 2 h / 60 °C View Scheme