Method for large-scale preparation of 5-amino-1-naphthyl nitrile

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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Problems solved by technology

[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%)

[0008] In summary, there are problems such as higher preparation cost of 5-amino-1-naphthalene nitrile (target object), harsh reaction conditions, and low yield of the target object in the prior art, resulting in 5-amino-1-naphthalene nitrile Difficult to scale up commercially

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