in N,N-dimethyl-formamide T=80°C; 1 h;

1: 70.5 percent / ozone, conc. HCl / H2O; methanol / -5 - 0 °C 2: 74.5 percent / dimethylformamide / 1 h / 80 °C View Scheme

2: 70.5 percent / ozone, conc. HCl / H2O; methanol / -5 - 0 °C 3: 74.5 percent / dimethylformamide / 1 h / 80 °C View Scheme

1: 1) conc. HCl, 2) NaHCO3 / 1) H2O, a) r.t., b) 80 deg C, 2) r.t. 3: 70.5 percent / ozone, conc. HCl / H2O; methanol / -5 - 0 °C 4: 74.5 percent / dimethylformamide / 1 h / 80 °C View Scheme

1: 1) conc. HCl, 2) NaHCO3 / 1) H2O, a) r.t., 2.5 h, b) 80 deg C, 40 min, 2) r.t., overnight 2: 17.2 percent / diisobutylaluminium hydride / CH2Cl2 / -60 °C 3: 11.9 percent / 1) n-butylamine, 1) ethylamine / ethanol / 32 h / Heating 4: 51.2 percent / Fe powder, FeCl2*(H2O)x, conc. HCl / ethanol; H2O / 1 h / Heating 5: 74.5 percent / dimethylformamide / 1 h / 80 °C View Scheme

1: 11.9 percent / 1) n-butylamine, 1) ethylamine / ethanol / 32 h / Heating 2: 51.2 percent / Fe powder, FeCl2*(H2O)x, conc. HCl / ethanol; H2O / 1 h / Heating 3: 74.5 percent / dimethylformamide / 1 h / 80 °C View Scheme

1: 17.2 percent / diisobutylaluminium hydride / CH2Cl2 / -60 °C 2: 11.9 percent / 1) n-butylamine, 1) ethylamine / ethanol / 32 h / Heating 3: 51.2 percent / Fe powder, FeCl2*(H2O)x, conc. HCl / ethanol; H2O / 1 h / Heating 4: 74.5 percent / dimethylformamide / 1 h / 80 °C View Scheme

sodium methylate in N,N-dimethyl-formamide T=80 - 90°C; 12 h;