反応 #813714

反応方程式

(2-amino-4-nitro-1-naphthylamino)-methanephosphonic acid diethyl ester

ethyloxalyl chloride

triethylamine

→

(6-Nitro-2,3-dioxo-1,2,3,4-tetrahydrobenzo[f]quinoxalin-1-yl)-methanephosphonic acid diethyl ester

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   その他to be completed at 55°
2. 2
   濃縮The batch is concentrated by evaporation
3. 3
   洗浄washed with brine
4. 4
   その他dried
5. 5
   その他The crude product is chromatographed on silica gel with ethanol as mobile solvent
6. 6
   その他76 mg or 67% of theory of product is obtained as polar fraction

実験手順

100 mg of (2-amino-4-nitro-1-naphthylamino)-methanephosphonic acid diethyl ester is dissolved in a few ml of tetrahydrofuran and treated with 95 microliters of distilled ethyloxalyl chloride and 118 microliters of triethylamine at ice-bath temperature. The solution is stirred first to room temperature and then the reaction is allowed to be completed at 55° oil bath temperature. The batch is concentrated by evaporation, taken up in ethyl acetate and washed with brine, dried and spun in. The crude product is chromatographed on silica gel with ethanol as mobile solvent. 76 mg or 67% of theory of product is obtained as polar fraction. NMR (DMSO,Delta in ppm): 1.03 (6H tr), 3.8 (4H dq), 4.93 (2H d), 7.73 (2H dd), 8.2, 8.35, 8.47 each 1H.

出典