Method for synthesizing methylaminopyridine compound by one-step method

A methylaminopyridine and compound technology, applied in the field of methylaminopyridine raw material synthesis, can solve problems such as being unsuitable for industrial production, high reaction conditions, and many three wastes pollution, and achieve convenient product separation and purification, lower production costs, and high yields Effect

Active Publication Date: 2019-12-24
XIAN CATALYST NEW MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the synthesis methods of methylaminopyridine disclosed in the prior art generally have problems such as high requirements on reaction conditions, high pollution of three wastes, and low yield due to the need for multi-step reactions.
[0004]In recent years, the country has attached great importance to environmental protection issues, especially chemical production enterprises, which are the key objects of environmental protection supervision. The synthetic method of methylaminopyridine disclosed in the prior art , the cost of the three wastes in the later stage is high, and the waste of resources is relatively serious, so it is not suitable for industrial production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] A method for synthesizing an aminopyridine compound in one step, comprising the following steps:

[0025] Use cyanopyridine as raw material, methanol as reaction solvent, and palladium carbon catalyst as catalyst. After nitrogen replacement, react for 4-10 hours under ammonia atmosphere, hydrogen pressure 0.5-2.0MPa, temperature 15-30°C, and cool to room temperature Filtrate, recover the filter residue for later use, and distill the filtrate under reduced pressure at 65°C and -0.1MPa to obtain the product aminopyridine compound;

[0026] Wherein, the mass ratio of cyanopyridine, methanol, palladium carbon catalyst, and ammonia is 1: (5-10): (0.01-0.05): (0.1-0.3);

[0027] The loading amount of palladium in the palladium-carbon catalyst is 5-10%, and the palladium-carbon catalyst prepared by the prior art can be used.

Embodiment 2

[0029] The method for synthesizing 4-methylaminopyridine by one-step method comprises the following steps:

[0030] (1) Add 200kg of 4-cyanopyridine and 1000kg of methanol into the pressure reactor, stir and dissolve and add 2kg of palladium-carbon catalyst with a palladium loading of 5%;

[0031] (2) After three replacements with nitrogen, 20kg of ammonia gas was introduced under stirring;

[0032] (3) Introduce hydrogen and react for 10 hours at a hydrogen pressure of 1.0MPa and a temperature of 30°C;

[0033] (4) After cooling to room temperature and filtering, the filter residue is recovered as a palladium carbon catalyst for later use; the filtrate is subjected to vacuum distillation at 65°C and -0.1MPa to obtain the product 4-methylaminopyridine, which is a colorless transparent viscous liquid, distilled out The reaction solvent methanol reclaims for subsequent use;

[0034] The yield of the product 4-methylaminopyridine was 82.65%, and its purity was 99.94% as detecte...

Embodiment 3

[0036] The method for synthesizing 4-methylaminopyridine by one-step method comprises the following steps:

[0037] (1) Add 200kg of 4-cyanopyridine and 1000kg of methanol into the pressure reactor, stir and dissolve and add 10kg of palladium-carbon catalyst with a palladium loading of 5%;

[0038] (2) After three replacements with nitrogen, 20kg of ammonia gas was introduced under stirring;

[0039] (3) Introduce hydrogen and react for 4 hours at a hydrogen pressure of 1.0MPa and a temperature of 30°C;

[0040] (4) After cooling to room temperature and filtering, the filter residue is recovered as a palladium carbon catalyst for later use; the filtrate is subjected to vacuum distillation at 65°C and -0.1MPa to obtain the product 4-methylaminopyridine, which is a colorless transparent viscous liquid, distilled out The reaction solvent methanol reclaims for subsequent use;

[0041] The yield of the product 4-methylaminopyridine was 89.93%, and its purity was 99.90% as detecte...

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Abstract

The invention discloses a method for synthesizing a methylaminopyridine compound by a one-step method. The method comprises the following steps: with cyanopyridine as a raw material, methanol as a reaction solvent and a palladium-carbon catalyst as a catalyst, performing nitrogen replacement, and carrying out a reaction for 4-10 hours in an ammonia atmosphere under the conditions that the hydrogenpressure is 0.5-2.0 MPa and the temperature is 15-30 DEG C; cooling the reaction product to room temperature, filtering the reaction product, recovering filter residues for later use, and performingreduced pressure distillation on the filtrate, thereby obtaining the product methylaminopyridine compound. The method provided by the invention has the advantages of mild reaction conditions, simple steps, convenient product separation and purification, few side reactions, high yield and the like, the purity of the final product is higher than 99.9%, and the catalyst filtered and recovered after the reaction and the distilled reaction solvent can be recycled, so that the problems of low yield, high cost and the like in the prior art are solved.

Description

technical field [0001] The invention belongs to the technical field of synthesis of methylaminopyridine raw materials, and in particular relates to a method for synthesizing methylaminopyridine compounds in one step. Background technique [0002] 4-Methylaminopyridine (CAS No.: 3731-53-1), density: 1.053g / cm 3 , melting point: -8°C (lit.), boiling point: 230°C at 760 mmHg, flash point: 108.3°C, as one of the methylaminopyridine compounds, it is an important class of chemical raw material intermediates, widely used in pesticides , medicine and life science and other fields, has broad application prospects. [0003] There are many methods for synthesizing methylaminopyridine. For example, Kaczmarek, Lukasz, Balicki, RomanJournal fuer Praktische Chemie / Chemiker-Zeitung, 1994 , vol. 336, #8 p. The reaction gives 4-methylaminopyridine. However, the synthesis methods of aminopyridine disclosed in the prior art generally have problems such as high requirements on reaction condit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/74
CPCC07D213/74Y02P20/584
Inventor 张宇高武校大伟姚琪黄琼淋李小安
Owner XIAN CATALYST NEW MATERIALS CO LTD
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