1: 2-amino-6-chloro-benzoic acid With sodium hydride in N,N-dimethyl-formamide T=20°C; 0.5 h; 2: ethyl iodide in N,N-dimethyl-formamide T=20°C; 48 h;

1: 2-amino-6-chloro-benzoic acid With 1,1'-carbonyldiimidazole in tetrahydrofuran 4 h; 2: ethanol; sodium ethanolate in tetrahydrofuran T=70°C; 1 h;

titanium(III) chloride; acetic acid 0.15 h; Ambient temperature;

1: 1.) aq. NaNO2, H2SO4 / 2.) 120 deg C, 1 h 2: 81 percent / K2CO3 / acetone / 3.5 h / Heating 3: 98 percent / 10percent aq. KOH / 3 h / Heating View Scheme

1: With sulfuric acid; sodium nitrite in water T=0°C; 0.333333 h; 2: in water T=120°C; 1 h;

sodium nitrite in water; Petroleum ether

1.1: H2SO4; NaNO2 / H2O / 0.33 h / 0 °C 1.2: 77 percent / H2O / 1 h / 120 °C 2.1: 88 percent / 1,5,7-triazabicyclo[4.4.0]dec-5-ene / acetonitrile / 20 h / 20 °C 3.1: 71 percent / 1 h / 230 °C 4.1: O3 / methanol / 0.5 h / -78 °C 4.2: dimethyl sulfide / methanol / -78 - 20 °C 5.1: 5.9 g / H3PO4 / H2O / 0.33 h / 100 °C 6.1: 90 percent / KOH / methanol; H2O / 1 h / Heating View Scheme

1.1: H2SO4; NaNO2 / H2O / 0.33 h / 0 °C 1.2: 77 percent / H2O / 1 h / 120 °C 2.1: 88 percent / 1,5,7-triazabicyclo[4.4.0]dec-5-ene / acetonitrile / 20 h / 20 °C 3.1: 71 percent / 1 h / 230 °C 4.1: O3 / methanol / 0.5 h / -78 °C 4.2: dimethyl sulfide / methanol / -78 - 20 °C 5.1: 5.9 g / H3PO4 / H2O / 0.33 h / 100 °C View Scheme

1.1: H2SO4; NaNO2 / H2O / 0.33 h / 0 °C 1.2: 77 percent / H2O / 1 h / 120 °C 2.1: 88 percent / 1,5,7-triazabicyclo[4.4.0]dec-5-ene / acetonitrile / 20 h / 20 °C 3.1: 71 percent / 1 h / 230 °C 4.1: O3 / methanol / 0.5 h / -78 °C 4.2: dimethyl sulfide / methanol / -78 - 20 °C 5.1: 5.9 g / H3PO4 / H2O / 0.33 h / 100 °C 6.1: 90 percent / KOH / methanol; H2O / 1 h / Heating 7.1: DPPA; Et3N; t-BuOH / 18 h / Heating 7.2: TFA / CH2Cl2 / 1 h / 0 °C View Scheme