1: With thionyl chloride 0.5 - 0.583333 h; Heating / reflux; 2: With AlCl3, aluminium chloride in nitrobenzene T=85°C; Friedel Crafts Acylation; 1.5 h; Product distribution / selectivity;

aluminium trichloride in 1,2-dichloro-ethane 6 h; Ambient temperature;

n-butyllithium in tetrahydrofuran; hexane T=-78°C; 4 h;

1: 59 percent / hydrogen chloride / methanol; benzene / 0.5 h / Ambient temperature 2: n-butyllithium / tetrahydrofuran; hexane / 4 h / -78 °C View Scheme

T=100°C;

unter Luftausschluss;

1: 85 percent / BF3*Et2O / 20 h / Heating 2: NaBH4 / methanol / Ambient temperature 3: 83 percent / p-tuluenesulfonic acid / benzene / 10 h / Heating View Scheme

1: 5.75 g / H2SO4 / 16 h / Heating 2: 91 percent / H2NOH*HCl; NaOAc / aq. ethanol / 1 h / Heating View Scheme

1: 1-carboxy-3-indanone; 1-(pyrrolidin-1-yl)methyl-1,2,3,4-tetrahydroisoquinoline With 4-(N,N-dimethlyamino)pyridine in dichloromethane T=0°C; 0.5 h; 2: dicyclohexyl-carbodiimide in dichloromethane

1: 80 percent / concd. H2SO4 / 10 h / Heating 2: 73 percent / 98percent H2SO4, 65percent aq. HNO3 / nitromethane / 0.25 h / -10 - -5 °C 3: 83 percent / perchloric acid, H2 / 10percent Pd/C / acetic acid / 6 h / 3102.9 Torr 4: 1.) aq. concd. HCl, NaNO2, 2.) CuCl2 / 1.) -5 to 0 deg C, 1 h, 2.) RT, 3 h 5: 92 percent / NH3(gas) / methanol / 168 h / Ambient temperature 6: 90 percent / Et3N, trichloroacetyl chloride / CH2Cl2 / 0 °C View Scheme