AR101137A1 - PROCESS FOR THE PREPARATION OF 4-ALCOXI-3-HYDROXIPICOLINIC ACIDS - Google Patents
PROCESS FOR THE PREPARATION OF 4-ALCOXI-3-HYDROXIPICOLINIC ACIDSInfo
- Publication number
- AR101137A1 AR101137A1 ARP150102187A ARP150102187A AR101137A1 AR 101137 A1 AR101137 A1 AR 101137A1 AR P150102187 A ARP150102187 A AR P150102187A AR P150102187 A ARP150102187 A AR P150102187A AR 101137 A1 AR101137 A1 AR 101137A1
- Authority
- AR
- Argentina
- Prior art keywords
- mixture
- formula
- compound
- prepared
- steps
- Prior art date
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- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Abstract
Se puede preparar 4,6-dibromo-3-hidroxipicolinonitrilo a partir de furfural en una serie de pasos químicos seleccionados de una aminación de ciano, la formación de sal de amina y una redisposición de bromación. Se pueden preparar convenientemente ácidos 4-alcoxi-3-hidroxipicolínicos a partir de 4,6-dibromo-3-hidroxipicolinonitrilo en una serie de pasos químicos seleccionados de una sustitución de bromo, una hidrólisis de nitrilo y reducción de halógeno. Se reivindican compuestos intermediarios. Reivindicación 1: Un proceso bifásico para la preparación del compuesto de fórmula (1), que comprende los siguientes pasos: a) crear la primera mezcla mediante la combinación de un sistema bifásico de solventes orgánico-agua, una fuente de amoniaco, una fuente de cianuro y un furan-2-aldehído de fórmula (2); b) separar una segunda mezcla de la primera mezcla que contiene el compuesto de fórmula (3) en forma de una solución en el solvente orgánico; c) agregar una solución acuosa de un ácido mineral a la segunda mezcla para formar una tercera mezcla; d) separar una cuarta mezcla de la tercera mezcla que es una mezcla acuosa que contiene el compuesto de la fórmula (4), en la que X es Br, HSO₄, NO₃, o H₂PO₄; e) agregar un agente de bromación a la cuarta mezcla para formar una quinta mezcla; y f) aislar el compuesto de fórmula (1) de la quinta mezcla. Reivindicación 25: El compuesto de fórmula (5) se puede preparar en un proceso de un recipiente que comprende los siguientes pasos: a) crear una mezcla que contenga el compuesto de fórmula (6) donde R¹ es un alquilo C₁₋₃; una base fuerte, metal zinc, y agua; b) calentar la mezcla; y c) aislar el compuesto de fórmula (5) de la mezcla. Reivindicación 27: El compuesto de fórmula (6) donde R¹ es un alquilo C₁₋₃; se puede preparar en un proceso que comprende los siguientes pasos: a) crear una mezcla que contenga el alcóxido de metal álcali de fórmula: MOR¹ donde M es Na o K, y R¹ es un alquilo C₁₋₃; y el compuesto de fórmula (1); b) calentar la mezcla; c) aislar un compuesto de fórmula (6) de la mezcla.4,6-Dibromo-3-hydroxypolycinonitrile can be prepared from furfural in a series of chemical steps selected from a cyano amination, amine salt formation and bromination redisposition. 4-Alkoxy-3-hydroxypicolinic acids can be conveniently prepared from 4,6-dibromo-3-hydroxypolycinonitrile in a series of chemical steps selected from a bromine substitution, a nitrile hydrolysis and halogen reduction. Intermediate compounds are claimed. Claim 1: A biphasic process for the preparation of the compound of formula (1), comprising the following steps: a) creating the first mixture by combining a biphasic system of organic solvents-water, a source of ammonia, a source of cyanide and a furan-2-aldehyde of formula (2); b) separating a second mixture from the first mixture containing the compound of formula (3) in the form of a solution in the organic solvent; c) adding an aqueous solution of a mineral acid to the second mixture to form a third mixture; d) separating a fourth mixture from the third mixture which is an aqueous mixture containing the compound of the formula (4), wherein X is Br, HSO₄, NO₃, or H₂PO₄; e) adding a brominating agent to the fourth mixture to form a fifth mixture; and f) isolating the compound of formula (1) from the fifth mixture. Claim 25: The compound of formula (5) can be prepared in a process of a container comprising the following steps: a) creating a mixture containing the compound of formula (6) wherein R¹ is a C₁₋₃ alkyl; a strong base, zinc metal, and water; b) heat the mixture; and c) isolate the compound of formula (5) from the mixture. Claim 27: The compound of formula (6) wherein R¹ is a C₁₋₃ alkyl; It can be prepared in a process comprising the following steps: a) create a mixture containing the alkali metal alkoxide of the formula: MOR¹ where M is Na or K, and R¹ is a C₁₋₃ alkyl; and the compound of formula (1); b) heat the mixture; c) isolate a compound of formula (6) from the mixture.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462021876P | 2014-07-08 | 2014-07-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR101137A1 true AR101137A1 (en) | 2016-11-23 |
Family
ID=58699755
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP150102187A AR101137A1 (en) | 2014-07-08 | 2015-07-08 | PROCESS FOR THE PREPARATION OF 4-ALCOXI-3-HYDROXIPICOLINIC ACIDS |
| ARP150102189A AR101139A1 (en) | 2014-07-08 | 2015-07-08 | INTERMEDIARIES OF THE PROCESS TO PREPARE ACIDS 4-ALCOXI-3-HYDROXYPICOLINICS |
| ARP150102188A AR101138A1 (en) | 2014-07-08 | 2015-07-08 | PROCESS FOR THE PREPARATION OF 4-ALCOXI-3-HYDROXIPICOLINIC ACIDS |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP150102189A AR101139A1 (en) | 2014-07-08 | 2015-07-08 | INTERMEDIARIES OF THE PROCESS TO PREPARE ACIDS 4-ALCOXI-3-HYDROXYPICOLINICS |
| ARP150102188A AR101138A1 (en) | 2014-07-08 | 2015-07-08 | PROCESS FOR THE PREPARATION OF 4-ALCOXI-3-HYDROXIPICOLINIC ACIDS |
Country Status (1)
| Country | Link |
|---|---|
| AR (3) | AR101137A1 (en) |
-
2015
- 2015-07-08 AR ARP150102187A patent/AR101137A1/en active IP Right Grant
- 2015-07-08 AR ARP150102189A patent/AR101139A1/en active IP Right Grant
- 2015-07-08 AR ARP150102188A patent/AR101138A1/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| AR101139A1 (en) | 2016-11-23 |
| AR101138A1 (en) | 2016-11-23 |
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