Synthesis method of benzocaprolactam

A technology of benzocaprolactam and synthesis method, which is applied in the direction of organic chemistry, can solve the problems of dangerous materials, use, and high cost, and achieve the effects of low cost, simple post-processing operation, and high output

Active Publication Date: 2019-11-15
ASTATECH CHENGDU BIOPHARM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The technical problem to be solved by the present invention is that the existing synthetic method of benzocaprolactam cannot avoid the use of dangerous materials at low cost, and the pu

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  • Synthesis method of benzocaprolactam
  • Synthesis method of benzocaprolactam

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Embodiment 1

[0029] A kind of synthetic method of benzocaprolactam of the present invention comprises the following steps:

[0030] S1, using o-nitrotoluene as raw material, condensing reaction with acrylate under alkali catalysis to obtain o-nitrobenzene butyric acid or its ester;

[0031] S2. O-nitrophenylbutyric acid or its ester reduces the nitro group and closes the ring to obtain the target product. The reaction principle of the present invention is as figure 1 shown.

[0032] The concrete implementation mode of the present invention is:

[0033] Preparation of methyl o-nitrobenzenebutyrate: put 500 g of o-nitrotoluene, 20 g of methyl acrylate, and 1 g of a phase transfer catalyst (such as tetrabutylammonium bromide) into a four-necked flask; heat up to 35° C., and slowly add hydrogen dropwise Concentrated potassium hydroxide aqueous solution prepared with 13 g of potassium oxide; react for 1 hour after the dropwise addition, add 200 g of water, and separate layers to obtain an aq...

Embodiment 2

[0037] The concrete implementation mode of the present invention is:

[0038] Preparation of methyl o-nitrobenzenebutyrate: put 3000 g of o-nitrotoluene, 200 g of methyl acrylate, and 10 g of a phase transfer catalyst (such as tetrabutylammonium bromide) into a four-necked flask; heat up to 35 ° C, slowly dropwise add hydrogen to oxidize Concentrated potassium hydroxide aqueous solution prepared with 130g of potassium; after the dropwise addition, react for 1 hour, add dilute sulfuric acid to adjust the pH to 1; add 1000g of dichloromethane for extraction three times; combine dichloromethane, dry over sodium sulfate, concentrate to remove solvent, and vacuum distill In addition to o-nitrotoluene, the black oil obtained was methyl o-nitrobenzene butyrate, with a yield of 77% and a purity of 68% by HPLC; 1H NMR (400MHz, DMSO) δ1.90-1.97 (m, 2H), 2.32– 2.36(m,2H),2.84–2.88(m,2H),3.61(s,3H),7.29–7.32(m,2H),7.45–7.49(m,1H),7.81–7.83(d,1H);

[0039] Preparation of benzocaprolactam:...

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Abstract

The invention discloses a synthesis method of benzocaprolactam. The synthesis method comprises the following steps: S1, using o-nitrotoluene as a raw material, and carrying out a condensation reactionon the o-nitrotoluene and an acrylate under catalysis of an alkali to obtain o-nitrophenylbutyric acid or o-nitrophenyl butyrate; and S2, reducing nitro of the o-nitrophenylbutyric acid or o-nitrophenyl butyrate, and performing ring closing to obtain a target product, wherein nitro of the o-nitrophenylbutyric acid or o-nitrophenyl butyrate is reduced to obtain amino. According to the synthesis method, cheap chemical products are used as initial raw materials, so that cost is low; post-treatment operation is simple, and a qualified product can be obtained through a rectification mode or simplemodes such as extraction, crystallization, filtration and the like, so that industrial production is easy to realize.

Description

technical field [0001] The invention relates to a synthesis method, in particular to a synthesis method of benzocaprolactam. Background technique [0002] Benzocaprolactam is an important intermediate for the synthesis of drugs and biologically active substances. This intermediate can be used to synthesize tetrahydro-1-benzazepine or nitrotetrahydro-1-benzazepine, etc., and then synthesize some research and development medicine. It can also be used in the synthesis of mature drugs. For example, it was approved by the FDA in 1990, and the high blood pressure drug Benazepril, which has been maturely used for many years, can be synthesized with this intermediate. [0003] It has been reported that the synthesis and post-treatment methods of benzocaprolactam mostly use tetralone as the starting material, and the cost of the material is relatively high. Patent WO2004069245A1 mentions that tetralone is used as a starting material, and sodium azide is rearranged to prepare benzoc...

Claims

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Application Information

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IPC IPC(8): C07D223/16
CPCC07D223/16
Inventor 应忠华杜沪东郭鹏
Owner ASTATECH CHENGDU BIOPHARM CORP
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