water; nickel in ethanol 8 h; Heating;

water; nickel in ethanol 8 h; Heating;

1: 96 percent / active γ-MnO2 / CHCl3 / 1 h / Heating 2: 83 percent / NaH / dimethylformamide / 3 h / 100 °C 3: 97 percent / NaBH4 / methanol / 0.33 h / Ambient temperature 4: 98 percent / SOCl2 / 1.) 0 deg C, 30 min, 2.) RT, 30 min 5: 1.) butyllithium / 1.) hexane, THF, -78 deg C, 10 min, 2.)a) hexane, THF, -78 deg C, 1 h, b) -50 deg C, 20 h 6: 84 percent / 0.25 N aq. HCl / methanol / 1.5 h / Ambient temperature 7: 86 percent / 6 N aq. HCl / 1 h / Heating 8: 83 percent / H2O / Raney Ni / ethanol / 8 h / Heating View Scheme

1: 83 percent / NaH / dimethylformamide / 3 h / 100 °C 2: 97 percent / NaBH4 / methanol / 0.33 h / Ambient temperature 3: 98 percent / SOCl2 / 1.) 0 deg C, 30 min, 2.) RT, 30 min 4: 1.) butyllithium / 1.) hexane, THF, -78 deg C, 10 min, 2.)a) hexane, THF, -78 deg C, 1 h, b) -50 deg C, 20 h 5: 84 percent / 0.25 N aq. HCl / methanol / 1.5 h / Ambient temperature 6: 86 percent / 6 N aq. HCl / 1 h / Heating 7: 83 percent / H2O / Raney Ni / ethanol / 8 h / Heating View Scheme

1: 86 percent / 6 N aq. HCl / 1 h / Heating 2: 83 percent / H2O / Raney Ni / ethanol / 8 h / Heating View Scheme

1: 98 percent / 0.25 N aq. HCl / methanol / 1.5 h / Ambient temperature 2: 83 percent / 6 N aq. HCl / 1 h / Heating 3: 87 percent / H2O / Raney Ni / ethanol / 8 h / Heating View Scheme

1: methanol / und anschliessendes Behandeln mit SOCl2 in Benzol 2: DMF / und anschliessendes Erwaermen mit wss.HCl View Scheme

N,N-dimethyl-formamide und anschliessendes Erwaermen mit wss.HCl;

1: 39 percent / triethylamine / benzene / 2 h / Heating 2: 2.) 'constant boiling' hydrochloric acid / 1.) (DMF), 24 h, room temp., 2.) reflux, 24 h View Scheme

ammonia; sodium