反応 #657291

反応方程式

4-hydroxy-8-methoxy-1-methyl-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-2-one

nitric acid

→

8-Methoxy-1-methyl-3-nitro-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]decane-2,4-dione

溶媒

chloroform

chloroform

反応条件

後処理

1. 1
   workup.ADDITIONpoured on ice water (10 ml)
2. 2
   その他the layers were separated
3. 3
   抽出the water phase extracted with ethyl acetate (3×20 ml)
4. 4
   洗浄the combined organic phases washed with water (15 ml) and brine (15 ml)
5. 5
   乾燥dried over sodium sulfate
6. 6
   濃縮concentrated
7. 7
   その他The residue was purified by chromatography on silica gel (ethyl acetate/cyclohexane 1:3)

実験手順

To a solution of 4-hydroxy-8-methoxy-1-methyl-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-2-one (compound P2.2) (150 mg, 0.454 mmol) in chloroform (5 ml) at −5° C. was added fuming nitric acid (0.038 ml, 57.8 mg, 0.917 mmol) in chloroform (0.5 ml) dropwise. The reaction mixture was stirred at 0° C. for 30 minutes and at room temperature for three days, poured on ice water (10 ml), the layers were separated, the water phase extracted with ethyl acetate (3×20 ml), the combined organic phases washed with water (15 ml) and brine (15 ml), dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (ethyl acetate/cyclohexane 1:3). Yield: 90 mg of 8-methoxy-1-methyl-3-nitro-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]decane-2,4-dione (title compound P1.13) as a white solid, mp 127-129° C.

出典