A preparing process of 3-nitro-2-indolone derivatives
A technology for indolinone and derivatives, which is applied in the field of preparation of 3-nitro-2-indolinone derivatives, can solve problems such as mild reaction conditions, and achieve low cost, environmental friendliness, and simple synthesis and post-treatment processes Effect
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Embodiment 7
[0032] Example 7 Synthesis of 3-nitro 2-indolinone derivatives (I-2)
[0033]
[0034]Add 3-methyl 2-indolinone (0.2 mmol), tert-butyl nitrite (t-BuONO, 0.4 mmol) and 1,4-dioxane (2 mL) into a 10 mL schlenk bottle, and then the reactor Stir the reaction at 25°C, monitor the reaction process by TLC or GC, stop the reaction until the reaction raw material 3-methyl-2-indolinone is completely reacted, wash the reaction solution with saturated saline, recover the organic phase, water Phases were extracted with ethyl acetate, and the organic phases were combined; the organic phase was dried over anhydrous sodium sulfate, filtered, and distilled under reduced pressure, and the residue was separated by column chromatography (n-hexane / ethyl acetate) to obtain the target product 3-nitro- 2-indolinone derivative I-2, yield 71%, 1 H NMR (400MHz, CDCl 3 )δ: 8.65(s, 1H), 7.41-7.36(m, 2H), 7.13(t, J=8.0Hz, 1H), 7.00(d, J=8.0Hz, 1H), 2.04(s, 3H); 13 C NMR (100MHz, DMSO-d6) δ: 170.8, 143...
Embodiment 8
[0035] Example 8 Synthesis of 3-nitro-2-indolinone derivatives (I-3)
[0036]
[0037] 3-Ethyl-2-indolinone (0.2 mmol), tert-butyl nitrite (t-BuONO, 0.4 mmol) and 1,4-dioxane (2 mL) were added to a 10 mL schlenk bottle, and the reaction The device was placed at 25°C to stir the reaction, and the reaction process was monitored by TLC or GC. When the reaction raw material 3-ethyl-2-indolinone was completely reacted, the reaction was stopped. The reaction solution was washed with saturated brine, and the organic phase was recovered. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined; the organic phase was dried over anhydrous sodium sulfate, filtered, and distilled under reduced pressure, and the residue was separated by column chromatography (n-hexane / ethyl acetate) to obtain the target product 3-nitro -2-indolinone derivative I-3, yield 50%, 1 H NMR (400MHz, CDCl 3 )δ: 9.05(s, 1H), 7.41-7.36(m, 2H), 7.13(t, J=8.0Hz, 1H), 7.01(d, J=7.6H...
Embodiment 9
[0038] Example 9 Synthesis of 3-nitro-2-indolinone derivatives (I-4)
[0039]
[0040] To a 10 mL schlenk bottle was added 3-phenyl-N-methyl-2-indolinone (0.2 mmol), tert-butyl nitrite (t-BuONO, 0.4 mmol) and 1,4-dioxane (2 mL ), then the reactor is placed under the condition of 25 DEG C to stir the reaction, and the reaction process is monitored by TLC or GC, until the reaction raw material 3-phenyl-N-methyl-2-indolinone is completely reacted, the reaction is stopped, and the reaction solution is Wash with saturated brine, recover the organic phase, extract the aqueous phase with ethyl acetate, combine the organic phases; dry the organic phase over anhydrous sodium sulfate, filter, and distill under reduced pressure, and the residue is separated by column chromatography (n-hexane / acetic acid Ethyl ester) obtain target product 3-nitro-2-indolinone derivative I-4, yield 81%, 1 H NMR (400MHz, CDCl 3 )δ: 7.58(d, J=6.8Hz, 1H), 7.54-7.49(m, 3H), 7.46-7.39(m, 3H), 7.23(t, J=8.0...
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