Method for large-scale preparation of 5-amino-1-naphthyl nitrile
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A technology of naphthalene nitrile and amino group, applied in the field of large-scale preparation of 5-amino-1-naphthalene nitrile, can solve the problems of harsh reaction conditions, high preparation cost, low yield, etc., and achieves low price, simple operation, safety, and reaction. mild effects
Inactive Publication Date: 2013-02-13
EAST CHINA UNIV OF SCI & TECH
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[0007] The deficiency of this method is: the price of used starting material (naphthalene nitrile) is very expensive, intermediate product has (isomer) isomer (requiring column chromatography to separate), yield is lower (two-step reaction is respectively 40% and 90%)
[000
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Embodiment 1
[0021] (1) Preparation of 1-bromo-5-nitronaphthalene:
[0022]
[0023] Heat 500g of nitronaphthalene (2.89mol) to 80-85°C to melt into a deep red liquid, keep the temperature constant and slowly add 450g of liquid bromine (2.81mol) dropwise within 2-3 hours. A large amount of acid gas released by the reaction is collected with lye. After one hour of reaction, the heating was stopped, and the reaction solution was poured into about 3 liters of ice water, and a large amount of yellow precipitate was precipitated, which was vacuum filtered to obtain a yellow solid, which was recrystallized with ethanol. 343 g of yellow needle crystals were obtained. Yield: 47%.
[0024] (2) Preparation of 5-nitro-1-naphthalene nitrile:
[0025]
[0026] Dissolve 343g (1.36mol) of 1-bromo-5-nitronaphthalene, 125g (1.4mol) of cuprous cyanide, and 193g (1.4mol) of potassium carbonate in 1500ml of N,N-dimethylformamide (DMF) , heated for 12 hours, the reaction solution was poured into a la...
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Abstract
The invention relates to a method for large-scale preparation of 5-amino-1-naphthyl nitrile. The method mainly comprises the steps of: by adopting nitronaphthalene as a starting material, carrying out bromination reaction on nitronaphthalene, so as to obtain 5-bromine-1-nitronaphthalene; reacting 5-bromine-1-nitronaphthalene with cuprous cyanide to obtain 5-nitro-1-naphthyl nitrile; and finally reducing 5-nitro-1-naphthyl nitrile to obtain the target product 5-amino-1-naphthyl nitrile. The method has the advantages that: (1) the starting raw material (nitronaphthalene) is cheap; (2) the reaction condition is relatively mild; and (3) the operation is simple and safe (no column chromatography isolation is carried out, and hazardous reagents is avoided using), so that the method is the method easy for large-scale commercial preparation of 5-amino-1-naphthyl nitrile.
Description
technical field [0001] The invention relates to a method for large-scale preparation of naphthalene ring compounds, in particular to a method for large-scale preparation of 5-amino-1-naphthalene nitrile. Background technique [0002] 5-Amino-1-naphthonitrile is a dye and an intermediate (it can be used to prepare nitric oxide fluorescent probes and a series of other compounds). [0003] There are mainly two kinds of existing methods for preparing 5-amino-1-naphthalene nitrile, one of which is: taking naphthoic acid as starting material, and obtaining target (Schuster, I.I.Magn.Reson.Chem.1996,34 through three-step reaction) , 301-310; Repine, J.T., Johnson, D.S., White, A.D., Favor, D.A., Stier, M.A., Yip, J., Rankin, T., Ding, Q., Maiti, S.N., Tetrahedron Lett., 2007, 48, 5539-5541), the synthetic route is as follows: [0004] [0005] The defect of this method is that the price of used naphthoic acid (starting material) is relatively expensive, needs to use the strong...
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