insoluble solid the filtered solid was washed with ethanol 50 ml and the combined organic filtrate was added with k 2 co 3 69 g 0 5 mol under ice bath after stirred for 30 minutes the reaction mixture was treated with nabh 4 g 0 29 mol in batches stirred for another 30 minutes filtered and concentrated dichloromethane 200 ml and water 150 ml were added into the resulting mixture and the water phase was adjusted to a ph of 13 to 14 with naoh 50 in water and extracted with dichloromethane 150 ml u00d7 2 the combined organic phase was dried with anhydrous na 2 so 4 concentrated to about 250 ml and then treated with hydrochloride isopropanol to give compound iii in hydrochloride salt form 73 g 65 1 h nmr 300 mhz cdcl 3 u03b4 3 06 m 4h 2ch 2 3 92 s 2h ch 2 6 76 7 26 m 4h h on phenyl compound ii 21 g 0 1 mol was dissolved in ethanol 150 ml and fe powder 11 g was fed into the reaction solution in 3 portions interval time 30 minutes after stirred for 3 hours at 40 45 u00b0 c the reaction mixture was cooled and filtered to remove the fe powder and insoluble solid after concentrated the filtrate was diluted with water 500 ml and extracted with dichloromethane 3 u00d7 50 ml the water phase was adjusted.