Category: 73406-50-5

Electric Literature of 73406-50-5, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 73406-50-5, name is Ethyl 3-hydroxypicolinate. A new synthetic method of this compound is introduced below.

The reaction was performed under Ar atmosphere.A solution of ethyl 3-hydroxypicolinate (2.10 g, 12.6 mmol) and ethyl bromoacetate(1.60 mL, 14.4 mmol) in anhydrous acetone (25 mL) was treated with anhydrousK2003,stirred under reflux for 15 h and cooled down to 23 00. The mixture was filteredand the solvent evaporated. The residue was dissolved in CH2CI2 (100 mL), washed with water (3 x 50 mL), dried over anhydrous MgSO4, filtered and evaporated. Column chromatography (SiC2 EtOAc/Heptane 25:75 -> 40:60) gave Ethyl 3-(2-ethoxy-2- oxoethoxy)picolinate (2.42 g, 76%) as a colorless oil.1H NMR (400 MHz, Chloroform-o) 6 = 8.36 (dd, J= 4.5, 1.2 Hz, 1H, H-Ar), 7.39 (dd, J8.5, 4.5 Hz, 1H, H-Ar), 7.29 (dd, J= 8.6, 1.2 Hz, 1H, H-Ar), 4.74 (s, 2H, O-CH2C=O),4.47 (q, J= 7.1 Hz, 2H, O-CH2CH3), 4.27 (q, J= 7.1 Hz, 2H, O-CH2CH3), 1.44 (t, J=7.1 Hz, 3H, O-CH2CH3), 1.29 (t, J= 7.1 Hz, 3H, O-CH2CH3) ppm.MS (ESl+, H20/MeCN) mlz(%): 254.0 (100, [M + H]j.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,73406-50-5, Ethyl 3-hydroxypicolinate, and friends who are interested can also refer to it.

Reference:
Patent; EUROPEAN MOLECULAR BIOLOGY LABORATORY; WILL, David William; REID, George; CHARAPITSA, Iryna; LEWIS, Joe David; (187 pag.)WO2018/229193; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 73406-50-5, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 73406-50-5, name is Ethyl 3-hydroxypicolinate. A new synthetic method of this compound is introduced below.

The reaction was performed under Ar atmosphere.A solution of ethyl 3-hydroxypicolinate (2.10 g, 12.6 mmol) and ethyl bromoacetate(1.60 mL, 14.4 mmol) in anhydrous acetone (25 mL) was treated with anhydrousK2003,stirred under reflux for 15 h and cooled down to 23 00. The mixture was filteredand the solvent evaporated. The residue was dissolved in CH2CI2 (100 mL), washed with water (3 x 50 mL), dried over anhydrous MgSO4, filtered and evaporated. Column chromatography (SiC2 EtOAc/Heptane 25:75 -> 40:60) gave Ethyl 3-(2-ethoxy-2- oxoethoxy)picolinate (2.42 g, 76%) as a colorless oil.1H NMR (400 MHz, Chloroform-o) 6 = 8.36 (dd, J= 4.5, 1.2 Hz, 1H, H-Ar), 7.39 (dd, J8.5, 4.5 Hz, 1H, H-Ar), 7.29 (dd, J= 8.6, 1.2 Hz, 1H, H-Ar), 4.74 (s, 2H, O-CH2C=O),4.47 (q, J= 7.1 Hz, 2H, O-CH2CH3), 4.27 (q, J= 7.1 Hz, 2H, O-CH2CH3), 1.44 (t, J=7.1 Hz, 3H, O-CH2CH3), 1.29 (t, J= 7.1 Hz, 3H, O-CH2CH3) ppm.MS (ESl+, H20/MeCN) mlz(%): 254.0 (100, [M + H]j.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,73406-50-5, Ethyl 3-hydroxypicolinate, and friends who are interested can also refer to it.

Reference:
Patent; EUROPEAN MOLECULAR BIOLOGY LABORATORY; WILL, David William; REID, George; CHARAPITSA, Iryna; LEWIS, Joe David; (187 pag.)WO2018/229193; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 73406-50-5 ,Some common heterocyclic compound, 73406-50-5, molecular formula is C8H9NO3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Step 2 A mixture of ethyl 3-hydroxypicolinate (15 g, 900 mmol), tributylsilyl chloride (16.23 g, 110 mmol), imidazole (8.0 g, 120 mmol) in methylene chloride was stirred overnight under a nitrogen atmosphere. Water was added and the methylene chloride layer was separated and concentrated in vacuo. Purification on a silica gel column using ethyl acetate-hexane (1:4) as the eluant gave ethyl 3-(tributylsilyloxy)picolinate as a solid (20 g).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 73406-50-5, Ethyl 3-hydroxypicolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Syntex (U.S.A.) LLC; US6316464; (2001); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.73406-50-5, name is Ethyl 3-hydroxypicolinate, molecular formula is C8H9NO3, molecular weight is 167.162, as common compound, the synthetic route is as follows.Formula: C8H9NO3

3-Hydroxy-picolinic acid (15.6 g, 42.1 mmol), ethanol (360 mL), benzene (100 mL) and 98% sulfuric acid (6 mL) were heated under reflux for 40 h. After evaporation of the ethanol and benzene, the residue was dissolved in water, neutralized with sodium bicarbonate, and extracted with chloroform. The organic layer was dried (MgS04), filtered, and then the solvent was evaporated to give ethyl 3-hydroxy-picolinate as a brown oily residue (11.0 g).A mixture of ethyl 3-hydroxy-picolinate (11.0 g, 65.8 mmol), ethyl bromoacetate (12.1 g, 72.4 mmol) and anhydrous potassium carbonate (11.8 g, 85.5 mmol) in acetone (120 mL) was heated under reflux for 15 h. After cooling, the inorganic material separated by filtration. The filtrate was dissolved in chloroform, washed with water, then brine and dried (MgSO4), filtered, and the solvent was evaporated to give a brown oily residue. The residue was purified by flash chromatography using a gradient of ammoniated methanol in chloroform to give ethyl 2- (2-ethoxycarbonyl-3-pyridyloxy) acetate (13.7 g) as a yellow oil (13.7 g). Ethyl 2- (2-ethoxycarbonyl-3-pyridyloxy) acetate (13.6 g, 54.0 mmol) and sodium ethoxide (8. 08 g, 118.8 mmol) in toluene (200 mL) were heated under reflux for 18 h. After cooling, a precipitate was collected by filtration, dissolved in the minimum amount of hot water (about 300 mL), and acidified with acetic acid (6 mL). The resulting precipitate was filtered, and dried in vacuo to give ethyl 3-hydroxyfuro [3,2-b] pyridine-2-carboxylate as a solid (7.0 g). Ethyl 3-hydroxyfuro [3,2-b] pyridine-2-carboxylate (6.90 g, 25.8 mmol) was dissolved in 10% hydrochloric acid (50 mL), and heated under reflux for 3 h. Evaporation of the hydrochloric acid solution gave furo [3,2-b] pyridin-3 (2H)-one hydrochloride (9.0 g). A portion of the furo [3,2-b] pyridin-3 (2H) -one hydrochloride was converted to its free base by treatment with saturated sodium bicarbonate and extraction with chloroform in preparation for the following step. N, N-Diisopropylethylamine (1.08 g, 8.34 mmol) was added slowly to a solution of furo [3,2-b] pyridin-3 (2H) -one (1.40 g, 7.25 mmol) in dry dichloromethane (60 mL) under nitrogen at-10°r; C. Then trifluromethanesulfonic anhydride (2.45 g, 8.70 mmol) was added slowly. The mixture was warmed to RT, and stirred overnight. The reaction was quenched with water. The organic layer was washed with water and brine, dried (MgS04), and then the solvent was evaporated to give a brown oily residue, which was purified by flash chromatography using chloroform to give the sub-title compound (980 mg) as a light-brown oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,73406-50-5, Ethyl 3-hydroxypicolinate, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/42538; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 73406-50-5, Ethyl 3-hydroxypicolinate, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Computed Properties of C8H9NO3, blongs to pyridine-derivatives compound. Computed Properties of C8H9NO3

EXAMPLE 2 Preparation of ethyl 3-(4,6-dimethoxypyrimidin-2-yl)oxy picolinate (Compound No. 2) To 0.5 g of 60% sodium hydride, 50 ml of hexane was added, and subjected to decantation. Then, the mixture was suspended in 30 ml of dimethylformamide. To the dimethylformamide suspension, 1.9 g of ethyl 3-hydroxypicolinate was gradually added, and the 2.0 g of 2-chloro-4,6-dimethoxypyrimidine was added. The mixture was heated and stirred at a reaction temperature of from 130 to 140 C. for 4 hours. After cooling, the reaction solution was poured into water, and extracted with ethyl acetate. The extract was washed with water and dried over magnesium sulfate. Ethyl acetate was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 1.4 g of ethyl 3-(4,6-dimethoxypyrimidin-2-yl)oxy picolinate. (Yield: 40%, pale yellow liquid, refractive index nD20 =1.5389)

The synthetic route of 73406-50-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kumiai Chemical Industry Co., Ltd.; Ihara Chemical Industry Co., Ltd.; US4832729; (1989); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 73406-50-5, Adding some certain compound to certain chemical reactions, such as: 73406-50-5, name is Ethyl 3-hydroxypicolinate,molecular formula is C8H9NO3, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 73406-50-5.

To 3-hydroxypyridine-2-carboxylic acid (25 g, 179.5 mmol) in a 1 L dried flask was added 400 mL ethanol and 100 mL toluene followed by the addition of 10 mL sulfuric acid. The mixture was heated at reflux (95 C.) for 3 days. After cooling to rt, the mixture was concentrated to ¼ of its volume, and diluted with 600 mL ethyl acetate and 200 mL water. The aqueous layer was extracted with 200 mL ethyl acetate, and the combined organic layers were washed with sat NaHCO3 (3×200 mL), brine, and dried over Na2SO4. The solid was filtered off and the solvent was concentrated under reduced pressure to give 21.9 g of ethyl 3-hydroxypyridine-2-carboxylate (73%), which was used in the next step without purification. This ester (21.9 g, 131 mmol) was dissolved in pyridine and cooled to -40 C., followed by addition of trifluoromethanesulfonic anhydride (48 g, 170 mmol). The reaction mixture was then warmed to 0 C. for 30 min, and then warmed to rt for another 30 min. Water (100 mL) was added to quench the reaction. The mixture was extracted with ethyl acetate (3×200 mL), and the combined organic layers were washed with sat sodium bicarbonate (200 mL), water (200 mL), brine (200 mL), and dried over sodium sulfate. The solid was filtered off, and the solvent was removed under reduced pressure to give 39 g (99%) of desired product, which was used in the next step without further purification. 1H NMR (300 MHz, CD2Cl2) delta 8.73 (dd, 1H), 7.72 (dd, 1H), 7.62 (dd, 1H), 4.46 (q, 2H), 1.42 (t, 3H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 73406-50-5, Ethyl 3-hydroxypicolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer Pharmaceuticals Corporation; US2005/192294; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 73406-50-5 ,Some common heterocyclic compound, 73406-50-5, molecular formula is C8H9NO3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

2-(Pyrrolidin-1-yl)carbonyl-3-hydroxy pyridine 18 g (0.093 moles) of ethyl-3-hydroxypicolinate [J. Heterocyclic Chem. 23 , 665, 1986] were cooled at -5C and ml 250 of pyrrolidine were added under nitrogen atmosphere. After the addition, the solution was allowed to reach room temperature, stirred 24 h and then evaporated in vacuo to give 15 g of the title compound as a slight yellow oil which crystallized on standing.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 73406-50-5, Ethyl 3-hydroxypicolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Smithkline Beecham Farmaceutici S.p.A.; EP447704; (1991); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 73406-50-5 ,Some common heterocyclic compound, 73406-50-5, molecular formula is C8H9NO3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

2-(Pyrrolidin-1-yl)carbonyl-3-hydroxy pyridine 18 g (0.093 moles) of ethyl-3-hydroxypicolinate [J. Heterocyclic Chem. 23 , 665, 1986] were cooled at -5C and ml 250 of pyrrolidine were added under nitrogen atmosphere. After the addition, the solution was allowed to reach room temperature, stirred 24 h and then evaporated in vacuo to give 15 g of the title compound as a slight yellow oil which crystallized on standing.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 73406-50-5, Ethyl 3-hydroxypicolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Smithkline Beecham Farmaceutici S.p.A.; EP447704; (1991); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 73406-50-5 ,Some common heterocyclic compound, 73406-50-5, molecular formula is C8H9NO3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

2-(Pyrrolidin-1-yl)carbonyl-3-hydroxy pyridine 18 g (0.093 moles) of ethyl-3-hydroxypicolinate [J. Heterocyclic Chem. 23 , 665, 1986] were cooled at -5C and ml 250 of pyrrolidine were added under nitrogen atmosphere. After the addition, the solution was allowed to reach room temperature, stirred 24 h and then evaporated in vacuo to give 15 g of the title compound as a slight yellow oil which crystallized on standing.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 73406-50-5, Ethyl 3-hydroxypicolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Smithkline Beecham Farmaceutici S.p.A.; EP447704; (1991); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 73406-50-5, Adding some certain compound to certain chemical reactions, such as: 73406-50-5, name is Ethyl 3-hydroxypicolinate,molecular formula is C8H9NO3, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 73406-50-5.

Intermediate 8. S-Trifluoromethanesulfonyloxy-pyridine^-carboxylic acid ethyl ester.; To a stirred solution of 3-hydroxy-pyridine-2-carboxylic acid ethyl ester (3.06 g, 20.0 mmol) and Et3N (triethylamine) (5.58 ml_, 40.0 mmol) in CH2CI2 (100 mL) at minus150C was added a solution of Tf2O (trifluoromethanesulfonic anhydride) (4.04 mL, 24.0 mmol) in CH2CI2 (10 mL). The reaction was stirred at this temperature for 1 hour and then CH2CI2 (100 mL) was added followed by H2O. The layers were separated and the organic EPO layer was washed three times with 30 ml H2O and twice with 30 ml brine. The organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica chromatography using a gradient of hexanes:EtOAc (100:0) to hexanes-.EtOAc (75:25) to yield 13.3 g (74.52%) of Intermediate 8 as a yellow oil.

According to the analysis of related databases, 73406-50-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2007/31828; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem