1: 6-Methoxyquinoline With boron trifluoride diethyl etherate in tetrahydrofuran T=0°C; 0.25 h; Inert atmosphere; 2: isopropylmagnesium chloride lithium chloride complex in tetrahydrofuran T=-50°C; 0.5 h; Inert atmosphere; 3: With chloranil in tetrahydrofuran T=20°C; 2 h; Inert atmosphere; regioselective reaction;

chloranil; trifluoroacetic anhydride in dichloromethane 12 h; Heating;

1: aq. NaOH 2: H2; HOAc / Pd/C / ethanol 3: NH2OH*HCl; pyridine / ethanol 4: 77 percent / (CF3CO)2O; 4-chloranil / CH2Cl2 / 12 h / Heating View Scheme

1: H2; HOAc / Pd/C / ethanol 2: NH2OH*HCl; pyridine / ethanol 3: 77 percent / (CF3CO)2O; 4-chloranil / CH2Cl2 / 12 h / Heating View Scheme

1: aq. NaOH 2: H2; HOAc / Pd/C / ethanol 3: NH2OH*HCl; pyridine / ethanol 4: 77 percent / (CF3CO)2O; 4-chloranil / CH2Cl2 / 12 h / Heating View Scheme

1: NH2OH*HCl; pyridine / ethanol 2: 77 percent / (CF3CO)2O; 4-chloranil / CH2Cl2 / 12 h / Heating View Scheme