of 8 bromo 2 bromomethylnaphthalene 29 6 g 0 0987 mol in acetonitrile 180 ml was added a solution of nacn 5 8 g 0 118 mol in h 2 o 20 ml the resulting mixture was heated under reflux for 1 hour 20 minutes the mixture was cooled concentrated and partitioned between ether and h 2 o the organic phase was washed with h 2 o saturated aqueous nahco 3 brine dried mgso 4 and concentrated to give a pale yellow solid 24 1 g 99 an analytical sample was obtained by recrystallization of 100 mg of similarly prepared material from toluene hexane m p 56 u00b0 c nmr dmso d 6 400 mhz u03b44 32 s 2h 7 46 m 1h 7 58 dd j 8 4 hz 1 7 hz 1h 7 92 dd j 7 5 hz 1 0 hz 1h 8 00 d j 8 4 hz 1h 8 04 d j 8 4 hz 1h 8 14 s 1h anal calcd for c 12 h 8 brn c 58 56 h 3 28 n 5 69 to a stirred solution of 8 bromo 2 naphthalenylacetonitrile 24 1 g 0 0979 mol and hydroxylamine hydrochloride 13 6 g 0 196 mol in dmso 150 ml was added naome 25 wt in meoh 4 48 ml 0 196 mol the resulting mixture was heated to 80 u00b0 c for 1 hour 30 minutes the meoh was removed by rotary evaporation and h 2 o 400 ml was added to the remaining mixture after 30 minutes the resulting solid was collected by filtration and recrystallized from toluene to give a white solid 20 8 g 76 an analytical sample was obtained from previously prepared.