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Method for reducing aromatic nitro to arylamine
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A technology for aryl nitro and aryl amine, applied in the field of reducing aryl nitro to aryl amine, can solve problems such as poor selectivity, and achieve the effects of low cost, high yield and high selectivity
Active Publication Date: 2017-06-06
宜昌尚诺德生物医药科技有限公司
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However, these methods still have disadvantages: when H2 is used as the reducing agent, special high-pressure equipment and flammable gas are required, and there is a certain risk; when hydrazine hydrate is used as the reducing agent , if the compound contains carbon-carbon double bonds, carbon-carbon triple bonds, or aldehyde groups, the selectivity is poor
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[0064] Nitrobenzene (0.6mmol, 74.0mg), water (6mmol, 108.0mg), Pd / C (0.03mmol, 6.4mg) and tetrahydroxydiboron (1.5mmol, 134.5mg), toluene (1mL), under nitrogen protection , reacted at 50°C for 24h, TLC monitored the reaction, added 10mL of water, extracted with ethyl acetate (10mL×3), combined the organic phases, dried over anhydroussodiumsulfate, filtered, concentrated under reduced pressure, and separated by column chromatography (V petroleumether: V acetic acidEthyl ester=3:1), 34.6 mg of colorless liquid was obtained, namely, the target compound was obtained, and the yield was 62%. 1 H NMR (400MHz, CDCl 3 )δ:7.27-7.23(m,2H),6.86-6.83(m,1H),6.76(dd,J 1 =1.2Hz,J 2 =7.6Hz,2H),3.66(s,br,2H); 13 C NMR (100MHz, CDCl 3 )δ: 146.50, 129.38, 118.60, 115.18
[0068] Nitrobenzene (0.6mmol, 74.0mg), water (6mmol, 108.0mg), Pd / C (0.03mmol, 6.4mg) and tetrahydroxydiboron (1.5mmol, 134.5mg), tetrahydrofuran (1mL), under nitrogen protection , reacted at 50°C for 24h, TLC monitored the reaction, added 10mL of water, extracted with ethyl acetate (10mL×3), combined the organic phases, dried over anhydroussodiumsulfate, filtered, concentrated under reduced pressure, and separated by column chromatography (V petroleumether: V acetic acidEthyl ester=3:1), 32.4 mg of colorless liquid was obtained, namely, the target compound was obtained with a yield of 58%. 1 H NMR (400MHz, CDCl 3 )δ:7.27-7.23(m,2H),6.86-6.83(m,1H),6.76(dd,J 1 =1.2Hz,J 2 =7.6Hz,2H),3.66(s,br,2H); 13 C NMR (100MHz, CDCl 3 )δ: 146.50, 129.38, 118.60, 115.18
[0072] Nitrobenzene (0.6mmol, 74.0mg), Pd / C (0.03mmol, 6.4mg) and tetrahydroxydiboron (1.5mmol, 134.5mg), methanol (1mL), reacted at 50°C for 24h under nitrogen protection, monitored by TLC To react, add 10 mL of water, extract with ethyl acetate (10 mL×3), combine the organic phases, dry over anhydroussodiumsulfate, filter, concentrate under reduced pressure, and separate by column chromatography (V petroleumether:V ethyl acetate=3:1), 33.0 mg of a colorless liquid was obtained, that is, the target compound was obtained with a yield of 59%. 1 H NMR (400MHz, CDCl 3 )δ:7.27-7.23(m,2H),6.86-6.83(m,1H),6.76(dd,J 1 =1.2Hz,J 2 =7.6Hz,2H),3.66(s,br,2H); 13 C NMR (100MHz, CDCl 3 )δ: 146.50, 129.38, 118.60, 115.18
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Abstract
The invention relates to a method for reducing aromatic nitro to arylamine. The method comprises the following steps: (1) taking an aromatic nitro compound as a raw material, water as a hydrogen source, a palladium compound, cheap and easy to obtain, as a catalyst and tetrahydroxydiboron as an additive to reduce nitro to obtain a product; (2) taking the aromatic nitro compound as the raw material, a copper salt, cheap and easy to obtain, as the catalyst, the tetrahydroxydiboron as the additive to reduce the nitro to obtain a product; and (3) taking the aromatic nitro compound as the raw material, water as the hydrogen source, and the tetrahydroxydiboron as the additive, without needing a metal catalyst, to reduce the nitro to obtain a product. A preparation method for the arylamine, which is provided by the invention, is mild in reaction condition, low in costs, environment-friendly, high in yield, and suitable for industrial production.
Description
technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for reducing an aromatic nitro group to an aromatic amine. Background technique [0002] Aromatic amines are also important organic synthesis intermediates and raw materials, which can be used to synthesize pesticides, medicines, rubber additives, dyes and pigments, synthetic resins, textile additives, surfactants, photosensitive materials and other fine chemicals. In addition, aromatic amines are common structural units in many bioactive drugs. Such as ADHD drug Adderall XR, anti-enteritisdrug mesalamine, post-traumatic neuralgiadrug Lyrica and other drugs. [0003] Regarding the preparation of aromatic amine compounds, the main methods reported at present can be obtained by reducing the corresponding aromatic nitro compounds. The methods for reducing aromatic nitro compounds in industry mainly include metal (iron powder, zincpowder, etc.) redu...
Claims
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