trichlorophosphate in N,N-dimethyl-formamide T=75 - 85°C; 2 h;

1: 2-chloro-8-hydroxyquinoline With potassium carbonate in acetone T=20°C; Inert atmosphere; 2: methyl iodide in acetone T=20°C; 15 h; Inert atmosphere;

pyridine; trichlorophosphate in chlorobenzene 2 h; Heating;

1: AlCl3 / chlorobenzene 2: 95 percent / potassium carbonate / acetone / 2 h / Heating 3: 99 percent / phosphorus oxychloride, pyridine / chlorobenzene / 2 h / Heating View Scheme

1: K2CO3 / acetone; H2O 2: AlCl3 / chlorobenzene 3: 95 percent / potassium carbonate / acetone / 2 h / Heating 4: 99 percent / phosphorus oxychloride, pyridine / chlorobenzene / 2 h / Heating View Scheme

1: 95 percent / potassium carbonate / acetone / 2 h / Heating 2: 99 percent / phosphorus oxychloride, pyridine / chlorobenzene / 2 h / Heating View Scheme

T=160 - 180°C;

1: 82 percent / lithium tetramethylpiperidide, trimethyl borate / tetrahydrofuran / 2 h / -75 °C 2: 90 percent / 32percent peracetic acid / acetic acid / 2 h / Ambient temperature 3: 84 percent / Zn, AcOH / H2O / 2 h / 70 °C View Scheme

1: 82 percent / lithium tetramethylpiperidide, trimethyl borate / tetrahydrofuran / 2 h / -75 °C 2: 90 percent / 32percent peracetic acid / acetic acid / 2 h / Ambient temperature 3: 95 percent / potassium carbonate / acetone / 1.5 h / Heating 4: 65 percent / Zn, AcOH / H2O / 1.5 h / 70 - 75 °C 5: 70 percent / pyridine hydrochloride / 1 h / 200 - 220 °C View Scheme

1: 2-chloro-8-methoxyquinoline With lithium diisopropyl amide in tetrahydrofuran; cyclohexane T=-78°C; 1.25 h; 2: N,N-dimethyl-formamide in tetrahydrofuran; cyclohexane T=-78°C; 0.5 h;