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Method for preparing 2-chlorine-3-amino-4-picoline

A technology of picoline and amino, which is applied in the field of preparing 2-chloro-3-amino-4-picoline, can solve the problems of cumbersome steps, high cost, high equipment requirements, etc., and achieve mild reaction conditions, reasonable price, and raw materials Easy to get effect

Inactive Publication Date: 2013-01-30
LUDONG UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The raw materials of this method are not easy to get, and the steps are cumbersome. It needs to be chlorinated at the 2,6-position of the intermediate 2,6-dihydroxy-4-methyl-3-cyanopyridine, and then dechlorinated. Rechlorination at the 2-position with chlorine gas
2, 6-position chlorination and dechlorination reduction and selective 2-position chlorination steps, equipment requirements are relatively high, the cost is expensive, and the yield is unstable
However, the price of the raw material 4,4-dimethoxy-2-butanone is relatively high, and it is not suitable for long-term storage, which increases the difficulty of industrial production

Method used

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  • Method for preparing 2-chlorine-3-amino-4-picoline
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  • Method for preparing 2-chlorine-3-amino-4-picoline

Examples

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Effect test

Embodiment 1

[0041] (1) Preparation of N-nitro-4-picoline: First add 200mL trifluoroacetic anhydride (0.84mol) to the reaction kettle, stir and cool to 0°C, slowly add 33mL 4-picoline (0.34mol) dropwise , A yellow solid was produced. After the addition was complete, the stirring reaction was continued at 0° C. for 2 h. Afterwards, 38 mL of concentrated nitric acid (0.72 mol) was added dropwise, the reaction temperature was gradually raised to room temperature, and the reaction was continued to stir for 10 h to obtain a solution of N-nitro-4-picoline, which was directly entered into the next step without further treatment.

[0042] (2) Preparation of 3-nitro-4-picoline: Add the N-nitro-4-picoline reaction solution obtained in the previous step dropwise to 64g of frozen sodium pyrosulfate (0.34mol) and 500mL of aqueous solution , stirred at room temperature for 24h, adjusted the pH of the system with 25% NaOH aqueous solution=6-7, CH 2 Cl 2 The product was extracted, the extract was dried,...

Embodiment 2

[0046] Synthesize as the method and condition of embodiment 1, (1), (3), (4) step reaction is unchanged, only change sodium pyrosulfate into sodium sulfite in (2) step, obtain product 3-nitro-4-formazine The crude product of pyridine has a purity of 75.4% and a yield of 60.3%.

Embodiment 3

[0048] Synthesize as the method and condition of embodiment 1, (1), (3), (4) step reaction is unchanged, only change sodium pyrosulfate into sodium bisulfite in (2) step, obtain product 3-nitro- The crude product of 4-picoline has a purity of 79.2% and a yield of 62.5%.

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Abstract

The invention relates to a novel synthetic method for preparing 2-chlorine-3-amino-4-picoline, and belongs to a production process and corresponding various process conditions for preparing the 2-chlorine-3-amino-4-picoline by using 4-picoline as raw materials sequentially through four-step reaction: concentrated nitric acid nitration, sodium pyrosulfite nitro migration, catalyst catalytic hydrogenation and hydrogen peroxide and concentrated hydrochloric acid chlorination. The method has the beneficial effects that industrial products of 4-picoline are used as raw materials, the raw materials are easily obtained, the price is proper, the reaction condition is mild, and a novel and efficient new path is provided for the industrial production of the 2-chlorine-3-amino-4-picoline.

Description

technical field [0001] The present invention relates to a new synthetic method for preparing 2-chloro-3-amino-4-methylpyridine. Specifically, 4-methylpyridine is used as raw material for nitration with concentrated nitric acid, sodium pyrosulfite to transfer the nitro group, Catalyst catalytic hydrogenation, hydrogen peroxide and concentrated hydrochloric acid chlorination, four-step reaction to prepare 2-chloro-3-amino-4-picoline production process and corresponding various process conditions. Background technique [0002] 2-Chloro-3-amino-4-picoline is a key pharmaceutical intermediate for the synthesis of the anti-AIDS drug nevirapine. It is widely used in the synthesis and research and development of medicines, pesticides, and veterinary drugs, and has high application value and market value. The existing synthetic 2-chloro-3-amino-4-picoline has the following methods: [0003] The earliest report on the synthesis of 2-chloro-3-amino-4-methylpyridine was in 1980. Chapma...

Claims

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Application Information

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IPC IPC(8): C07D213/73
Inventor 刘刚马文泉李晓燕陈宏光刘新泳温全武
Owner LUDONG UNIVERSITY
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