1: quinoline, H2 / 10percent Pd/BaSO4 / methanol / 0.13 h / 93.09 Torr 2: 95 percent / (4-dimethylamino)pyridine (DMAP), pyridine / 0 °C View Scheme

dipyridinium dichromate in dichloromethane 24 h; Ambient temperature;

quinoline; hydrogen; Pd-BaSO4 in methanol P=93.09 Torr; 0.133333 h; Yield given. Yields of byproduct given;

2: 1) LDA / 1) -78 deg C 3: 94 percent / Et3N / (Ph3P)2PdCl2 / 75 °C 4: H2, Lindlar catalyst, quinoline / hexane 5: 2,2,4-trimethyl-pentane / Heating 6: 82 percent / ion-exchange resin AG 50W-X4 / methanol / 48 h / Ambient temperature; in the dark View Scheme

1: quinoline, H2 / 10percent Pd/BaSO4 / methanol / 0.13 h / 93.09 Torr 2: 95 percent / (4-dimethylamino)pyridine (DMAP), pyridine / 0 °C 3: 1.) Cu2I2 / 1.) Et2O, 0 deg C, 30 min, 2.) Et2O, RT, 48 h 4: 100 percent / LiAlH4 / diethyl ether / 1 h / 0 °C 5: 100 percent / pyridinium dichromate, pyridinium p-toluenesulfonate / CH2Cl2 / 24 h / Ambient temperature 6: 1.) n-BuLi / 1.) hexane, THF, -70 deg C, 30 min, 2.) THF, -70 deg C, 90 min 7: 76 percent / AG-50WX4(resin) / methanol / 16 h / Ambient temperature View Scheme