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Preparation method of 1-nitro-2-naphthol derivative

A technology of naphthol derivatives and nitro, which is applied in the field of preparation of nitronaphthol derivatives, can solve problems such as inappropriate preparation of nitronaphthol derivatives, and achieve the effects of increasing yield and improving selectivity

Active Publication Date: 2017-06-13
NINGBO UNIV
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Problems solved by technology

[0007] But the contriver has run into difficulty when applying these reaction conditions to the nitration reaction of naphthol to prepare nitronaphthol, even under the same optimal condition reaction, the yield of the nitration reaction of naphthol is about 20% all the time It can be seen that due to the difference in the structure of the reaction substrate, the above-mentioned method disclosed in prior art documents 1-2 is also not suitable for the preparation of nitronaphthol derivatives

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  • Preparation method of 1-nitro-2-naphthol derivative
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  • Preparation method of 1-nitro-2-naphthol derivative

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Embodiment 17

[0040]Example 17 Synthesis of 6-bromo-1-nitro-2-naphthol

[0041]

[0042] Add 66.6mg (0.3mmol) of 6-bromo-2-naphthol, 61.8mg (0.6mmol) of tert-butyl nitrite, 10.8mg (0.6mmol) of water, and tetrahydrofuran (2mL) into a dry 10mL schlenk bottle. Stir at room temperature for 2.5h. After the reaction was completed, the reaction solution was filtered through a glass dropper containing silica gel, rinsed with ethyl acetate, the filtrate was spin-dried, and separated by column chromatography to obtain the target product, a yellow solid, with a yield of 93%. 1 H NMR (300MHz, CDCl 3 ): 12.13(s, 1H), 8.77(d, J=9.3Hz, 1H), 7.94-7.87(m, 2H), 7.78-7.74(m, 1H), 7.27(t, J=9.0Hz, 1H) ; 13 C NMR (75MHz, CDCl 3 ): 158.8, 138.0, 133.9, 131.2(2), 129.9, 125.5, 125.1, 120.8, 119.5; IR (KBr, cm -1 ): 1538, 1361; LRMS (EI, 70eV) m / z (%): 269 (M+2, 21), 267 (M + , 22), 222(100), 115(97).

Embodiment 18

[0043] Example 18 Synthesis of 2-nitro-1-naphthol

[0044]

[0045] Add 43.2 mg (0.3 mmol) of 1-naphthol, 61.8 mg (0.6 mmol) of tert-butyl nitrite, 10.8 mg (0.6 mmol) of water, and tetrahydrofuran (2 mL) into a dry 10 mL schlenk bottle, and stir the reaction bottle at room temperature 4h. After the reaction was completed, the reaction solution was filtered through a glass dropper containing silica gel, rinsed with ethyl acetate, the filtrate was spin-dried, and separated by column chromatography to obtain the target product, a yellow solid, with a yield of 82%. 1 H NMR (300MHz, CDCl 3 ): 12.23(s, 1H), 8.49(d, J=8.1Hz, 1H), 7.98(d, J=9.6Hz, 1H), 7.80(d, J=7.8Hz, 1H), 7.71(t, J =7.5Hz, 1H), 7.61(t, J=7.5Hz, 1H), 7.32(d, J=9.3Hz, 1H); 13 C NMR (75MHz, CDCl 3 ): 155.7, 138.7, 137.4, 131.4, 127.9, 127.1, 126.5, 125.1, 120.2, 119.4; IR (KBr, cm -1 ): 1540, 1370; LRMS (EI, 70eV) m / z (%): 189 (M + , 100), 115(74), 89(34).

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Abstract

The invention belongs to the field of organic synthesis and in particular relates to a preparation method of a 1-nitro-2-naphthol derivative. The preparation method comprises the following steps: adding a 2-naphthol derivative shown as a formula I-1, tert-butyl nitrite and a certain amount of water into a dry reactor; adding a certain amount of an organic solvent and stirring at room temperature (commonly referring to 20 DEG C to 25 DEG C) for a period of time; after reacting, filtering an reaction solution through a glass dropper filled with silica gel; washing a filter cake with ethyl acetate; spinning and drying filtrate; carrying out silica gel column chromatography separation to obtain a target product with a formula I. A reaction formula can be shown in the description.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of nitronaphthol derivatives. Background technique [0002] Nitronaphthol is an important class of organic synthesis intermediates and pharmaceutical intermediates. The classic methods for synthesizing nitronaphthol in the prior art include oxidation of nitrosonaphthol, hydroxylation of nitronaphthalene, nitration of naphthol and hydrolysis of 1-chloro-2 nitronaphthalene, etc. But there are many shortcomings in these traditional methods, with regard to the method for the nitration reaction of naphthol to prepare nitronaphthol, the nitration reagent used in the prior art comprises sodium nitrite, isoamyl nitrite, nitro tetrahalogen ring Hexadienone, ceric ammonium nitrate, etc. These methods usually generate a mixture of o- and p-nitronaphthols and polynitrophenols, resulting in difficult purification of the target product and low yield. Although...

Claims

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Application Information

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IPC IPC(8): C07C201/08C07C205/25C07C205/26
CPCC07C201/08C07C205/25C07C205/26
Inventor 朱文明魏文廷梁炜达应炜炜黄依铃吴益杨晨光
Owner NINGBO UNIV
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