1: 97.6 percent / Cu / quinoline / 2 h / Heating 2: 1.) POCl3, 3.) aq. NaOH 3: 1.) NaH / 1.) THF, 40 deg C, 90 min, 2.) THF, RT, 18 h View Scheme

1: 93.9 percent / 2N aq. NaOH / 0.5 h / Heating 2: 97.6 percent / Cu / quinoline / 2 h / Heating 3: 1.) POCl3, 3.) aq. NaOH 4: 1.) NaH / 1.) THF, 40 deg C, 90 min, 2.) THF, RT, 18 h View Scheme

1: 89 percent / xylene / 9 h / Heating 2: 93.9 percent / 2N aq. NaOH / 0.5 h / Heating 3: 97.6 percent / Cu / quinoline / 2 h / Heating 4: 1.) POCl3, 3.) aq. NaOH 5: 1.) NaH / 1.) THF, 40 deg C, 90 min, 2.) THF, RT, 18 h View Scheme

1: 97 percent / NaOMe / methanol / 2 h / -8 - -5 °C 2: 89 percent / xylene / 9 h / Heating 3: 93.9 percent / 2N aq. NaOH / 0.5 h / Heating 4: 97.6 percent / Cu / quinoline / 2 h / Heating 5: 1.) POCl3, 3.) aq. NaOH 6: 1.) NaH / 1.) THF, 40 deg C, 90 min, 2.) THF, RT, 18 h View Scheme

1: 1.) POCl3, 3.) aq. NaOH 2: 1.) NaH / 1.) THF, 40 deg C, 90 min, 2.) THF, RT, 18 h View Scheme

sodium hydride 1.) THF, 40 deg C, 90 min, 2.) THF, RT, 18 h; Yield given. Multistep reaction;

1.1: 57 percent / t-BuOK / tetrahydrofuran 2.1: LDA / tetrahydrofuran / 1 h / -78 °C 2.2: tetrahydrofuran / -78 - -10 °C 2.3: 56 percent / NH2OH*HCl; AcONa / 1,2-dichloro-benzene / 8 h / Heating View Scheme