was added water until the solution turned slightly cloudy 150 ml methoxylamine hydrochloride 8 723 g 102 35 mmol was added and the mixture was stirred overnight the methanol was removed under vacuum and the residue was extracted with ch 2 cl 2 and dried over mgso 4 the product was purified by flash chromatography on silicagel ch 2 cl 2 hexanes 1 3 to give 8 as a light orange powder in 60 yield mp 121 124 u00b0 c 1 h nmr 400 mhz dmso d 6 u03b4 1 95 s 4h 3 25 s 4h 3 93 s 3h 4 61 s 2h 6 53 s 2h 7 52 s 2h fabhrms found m 296 0522 calcd for c 13 h 17 on 2 br m 296 0519 a solution of quinoline 149 u03bcl 1 26 mmol and 8 486 mg 1 64 mmol was refluxed in acetone 4 ml for 5 days a dark red solid was separated by filtration in 61 yield mp 178 180 u00b0 c 1 h nmr 400 mhz dmso d 6 u03b4 1 90 s 4h 3 15 s 4h 3 99 s 3h 6 39 m 4h 7 36 d 2h j 7 3 hz 8 05 t 1h j 7 0 hz 8 18 m 1h 8 30 m 2h 8 46 d 1h j 8 1 hz 9 29 d 1h j 8 1 hz 9 65 d 1h j 5 1 hz fabhrms found m 346 1920 calcd for c 22 h 24 on 3 m 346 1914 the title compound was prepared following the examples herein above using suitable reagents 39 yield mp 169.