thionyl chloride in N,N-dimethyl-formamide; toluene T=0 - 5°C;

1: K2CO3 / acetone; dimethylformamide / 72 h / Heating 2: SOCl2, DMF / CH2Cl2 / 16 h / Ambient temperature View Scheme

1.1: sodium amide / N,N-dimethyl-formamide / 0.25 h / 10 - 15 °C 1.2: 10 - 15 °C 2.1: hydrogen / palladium on carbon / tetrahydrofuran; methanol / 4 h / 2206.72 - 3677.86 Torr 3.1: palladium hydroxide on carbon / 45 - 50 °C / 3677.86 - 5884.58 Torr View Scheme