Process for the synthesis of diaminopyridine and related compounds

A technology for compound and reaction mixture, applied in the field of synthesizing diaminopyridine and related compounds, can solve the problems of difficulty, inadvisability, low commercial feasibility of yield and the like

Inactive Publication Date: 2010-07-21
EI DU PONT DE NEMOURS & CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Larger amounts of copper or aluminum powder and higher temperatures and pressures are required to carry out this reaction, making

Method used

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  • Process for the synthesis of diaminopyridine and related compounds
  • Process for the synthesis of diaminopyridine and related compounds
  • Process for the synthesis of diaminopyridine and related compounds

Examples

Experimental program
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Embodiment 1

[0076] In a 600mL autoclave equipped with an air-entraining stirrer, add 5g of CuI in 120g of ammonia (30% by weight NH 3 ) solution and mixed with 77 g ammonium acetate and 60 g 2,6-dichloropyridine. After purging with nitrogen, 24 g of liquid ammonia was added to bring the pressure to about 150 psi (1.03 MPa). Next, the reaction mixture was heated at 150 °C for 8 h with stirring. During the reaction, the pressure dropped from an initial pressure of 680 psi (4.69 MPa) to 450 psi (3.10 MPa). The reaction mixture was cooled to room temperature, and the pressure was returned to atmospheric. The reaction mixture was analyzed using quantitative GC analysis. The conversion rate of 2,6-dichloropyridine is greater than 99.5%. The reaction mixture contained 0.37 mol of 2,6-diaminopyridine and 0.03 mol of 2-chloro-6-aminopyridine. The yields of 2,6-diaminopyridine and 2-chloro-6-aminopyridine were 91% and 7%, respectively.

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Abstract

A process is provided for the synthesis of a diaminopyridine, such as 2, 6-diaminopyridine and related compounds, which are used industrially as compounds and as components in the synthesis of a variety of useful materials. The synthesis proceeds by means of a chlorine-ammonia displacement in the presence of a copper source.

Description

[0001] This patent application claims priority to US Provisional Application 60 / 953,261, filed August 1, 2007, which is hereby incorporated by reference in its entirety as a part hereof for all purposes. technical field [0002] The present invention relates to the preparation of diaminopyridines such as 2,6-diaminopyridine and related compounds, which are used industrially as precursors and intermediates in the synthesis of a variety of useful materials . Background of the invention [0003] Compound 2,6-diaminopyridine [0004] [0005] It is commonly used as a starting material for the preparation of a variety of products including dyes, metal ligands, pharmaceuticals, pesticides and monomers for incorporation into polymers such as those described in US 5,674,969. [0006] It is known that diaminopyridines can be prepared via a Chichibabin amination reaction in which pyridine is reacted with sodium amide in an organic solvent. This is a complex reaction requiring har...

Claims

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Application Information

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IPC IPC(8): C07D213/61C07D213/73
CPCC07D213/73
Inventor J·C·里特
Owner EI DU PONT DE NEMOURS & CO
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