hydrogen; iron(II) sulfate; palladium on activated charcoal 1) 50percent aq. ethanol, 18 h, 2a) heating in tetralin, 2b) 12 h, room temperature; Yield given. Multistep reaction;

1: 95 percent / conc. H2SO4 / 24 h / Heating 2: 1) H2, 2) 8 N NaNO2, acetic acid / 1)PtO2 / 1) acetic acid, 5 - 40 psi, 2) 48 h, water - actic acid 3: 1) H2, ferrous sulfate / 1) 10percent Pd/C / 1) 50percent aq. ethanol, 18 h, 2a) heating in tetralin, 2b) 12 h, room temperature View Scheme

1: 1) H2, 2) 8 N NaNO2, acetic acid / 1)PtO2 / 1) acetic acid, 5 - 40 psi, 2) 48 h, water - actic acid 2: 1) H2, ferrous sulfate / 1) 10percent Pd/C / 1) 50percent aq. ethanol, 18 h, 2a) heating in tetralin, 2b) 12 h, room temperature View Scheme

dimethyl amine T=-5 - 0°C; 0.5 h; Product distribution;

lithium aluminium tetrahydride in tetrahydrofuran 18 h; Heating;