sodium hydride in N,N-dimethyl-formamide T=20°C; 18 h; Product distribution / selectivity;

1: 70 percent / H2 / 10percent Pd/C / methanol / 0.75 h / 3361.5 Torr 2: 2) dilute HCl / 1) THF-ether, reflux, 2 h, 2) steam bath, 5 min View Scheme

dimethisoquin; copper 1.5 h; Heating;

hydrogenchloride 1) THF-ether, reflux, 2 h, 2) steam bath, 5 min; Yield given. Multistep reaction;

1: 1.) 30percent aq. KOH; 2.) 18percent aq. HCl / 1.) methanol-water, reflux, 2h 2: 75 percent / quinoleine, Cu powder / 1.5 h / Heating View Scheme

potassium tert-butylate in tetrahydrofuran 3 h; Heating;

1: 76 percent / potassium t-butoxide / tetrahydrofuran / 3 h / Heating 2: 77 percent / 2-pyrrolidinone hydrotribromide, pyrrolidinone / tetrahydrofuran / 3 h / Heating View Scheme

1: 76 percent / potassium t-butoxide / tetrahydrofuran / 3 h / Heating 2: 77 percent / 2-pyrrolidinone hydrotribromide, pyrrolidinone / tetrahydrofuran / 3 h / Heating 3: tetrahydrofuran / 1 h / ice bath 4: NaBH4 / methanol View Scheme

1: 76 percent / potassium t-butoxide / tetrahydrofuran / 3 h / Heating 2: 77 percent / 2-pyrrolidinone hydrotribromide, pyrrolidinone / tetrahydrofuran / 3 h / Heating 3: tetrahydrofuran; H2O / 0.33 h / ice bath 4: NaBH4 / methanol; tetrahydrofuran; H2O / 0.25 h 5: 92 percent / K2CO3 / ethyl acetate; H2O / 0.08 h / ice bath 6: 87 percent / potassium t-butoxide / tetrahydrofuran / 0.33 h / Ambient temperature 7: 83 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating View Scheme

1: 76 percent / potassium t-butoxide / tetrahydrofuran / 3 h / Heating 2: 77 percent / 2-pyrrolidinone hydrotribromide, pyrrolidinone / tetrahydrofuran / 3 h / Heating 3: tetrahydrofuran / 1 h / ice bath 4: NaBH4 / methanol View Scheme