CN110028445A - A kind of process using carbon dioxide production 3- Ethyl formate -4- hydroxyl -2- pyridone - Google Patents
A kind of process using carbon dioxide production 3- Ethyl formate -4- hydroxyl -2- pyridone Download PDFInfo
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/69—Two or more oxygen atoms
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Abstract
A kind of process using carbon dioxide production 3- Ethyl formate -4- hydroxyl -2- pyridone, steps are as follows: claiming disubstituted-4-hydroxy -6- alkyl -2- pyridinone substrate, catalyst and potassium tert-butoxide in Schleck bottles, degassing is continually fed into the carbon dioxide of 1atm.Solvent is added, reacts in oil bath.After the reaction was completed, it post-processes, obtains -4 hydroxyl -2- pyridine compounds 2 of 3- carboxyl.Obtained compound 2, (1- (3- dimethylamino-propyl) -3- ethyl-carbodiimide hydrochloride) and 2- methylamino pyridine and ethyl alcohol are subjected to esterification.After having reacted, column chromatography for separation obtains 3- Ethyl formate -4- hydroxyl -2- pyridone 3.The present invention is extensive using catalyst source, cheap；Preparation process is simple, lower to equipment requirement, and raw material sources are extensive and at low cost, and toxicity is low, is easy to industrial amplification production.
Description
Technical field
The invention belongs to carbon dioxide utilization and 3- Ethyl formate -4- hydroxyl -2- pyridone preparation technical field,
It is related to a kind of preparation process using carbon dioxide production 3- Ethyl formate -4- hydroxyl -2- pyridone, and in particular to it is a kind of in N,
In dinethylformamide solution, 4- hydroxyl -2- pyridine compounds and carbon dioxide occur addition reaction and generate 3- carboxyl -
The process of 4- hydroxyl -2- pyridone.And further synthesis one kind has widely applied 3- formic acid using obtained acid
The process of ethyl ester -4- hydroxyl -2- pyridone.
Background technique
Currently, global carbon dioxide discharge is exceeded, greenhouse effects are caused, bring very more adverse consequences.At present
Every country actively formulates corresponding measure, and energy-saving and emission-reduction are planted trees energetically, meanwhile, every country is also constantly being
It realizes blue mountains and green waters and struggles, no longer using GDP as No.1 target, but in conjunction with environment, reduce carbon dioxide as far as possible
And the discharge of trade waste.However, social progress be unable to do without flourishing for industry, how carbon dioxide become one
The energy of kind clean and effective is the mainstream of current era, and having a large amount of scientists is to realize that the recycling of carbon dioxide has been paid largely
Time and efforts.Carbon dioxide is based on the inherent advantage of oneself, and renewable, suitable carbon dioxide does not have toxic side effect, and
It has been a kind of good C1 resource in fact by the testimony of a witness, the carbochain that extends can be used to, part scientist is by carbon dioxide transitions
For many industrial products or industrialization intermediate feed, there are many more the scientists in research material direction by carbon dioxide transitions
The resource that can be recycled for methanol, carbon monoxide etc..However, the development of carbon dioxide at present, there are many deficiencies, conversion ratios
Not high, the type of conversion is very little, the conversions of many carbon dioxide can not industrial applications, therefore, a large amount of researcher is thrown
Enter into the trans-utilization of carbon dioxide, expand the use pattern of carbon dioxide, improves the efficiency of catalysis transform of carbon dioxide,
Under the premise for guaranteeing industrial development, so that carbon dioxide will not threaten.
4- hydroxyl -2- pyridine compounds are a kind of important alkaloids, and 1864, Tuson was separated from castor bean
A kind of toxic compound recinine is obtained, 4- hydroxyl -2- pyridinone alkaloid has been started in the discovery of this compound
The beginning.Due to 4- hydroxyl -2- pyridine compounds antimycotic, antibacterium, desinsection and in terms of have it is very strong
Bioactivity, so attention of this kind of compound by more and more scientists.Much contain 4- hydroxyl -2- pyridone parent
The alkaloid of structure has antitumor, antimycotic bioactivity, their synthetic method is also widely studied.With people
The demand of anti-tumor drug and antifungal drug is continued to increase, study 4- hydroxyl -2- pyridine compounds structure with
Medicine efficacy relation, exploitation newtype drug have great importance.4- hydroxyl -2- pyridine compounds still produce pyridines simultaneously
The important source material of compound, the position 3- and the position 5- of pyridine are difficult to be modified, and the 3- of 4- hydroxyl -2- pyridine compounds
Number there is active α-H, therefore, if addition reaction can be occurred for 4- hydroxyl -2- pyridine compounds and carbon dioxide,
It may be said that it is significant, it on the one hand can be used as the mode of a kind of the increase carbochain and functional group of the modification position pyridine 3-, it is another
Aspect also provides a kind of important means for developing new 4- hydroxyl -2- pyridine compounds.
Therefore, how environmental protection preparation and develop 4- hydroxyl -2- pyridine compounds and carbon dioxide generation addition it is anti-
It should be of great significance.
Summary of the invention
Present invention aim to address the recycling of environmental energy and the existing 4- hydroxyl -2- pyridinone targeteds of improvement
The problems such as conjunction object synthesis is complicated, Gao Chengben, to expand the chemical reaction type that carbon dioxide can occur, carries out carbon dioxide
Recycling recycles, and so as to the compound probability product of economical rationality multipath, provides one kind and utilizes titanium dioxide in atmospheric conditions
The method that carbon produces 3- Ethyl formate -4- hydroxyl -2- pyridone 3 (3a-3e).The invention is easy to operate, lower to equipment requirement,
Raw material sources are extensive and at low cost, and toxicity is low, and processing is simple, and synthesis condition is mild, and yield is higher, are easy to industrialize amplification, real
The preparation 3- Ethyl formate -4- hydroxyl -2- pyridone of more high-efficiency environment friendly is showed.
The technical scheme is that
A kind of process using carbon dioxide production 3- Ethyl formate -4- hydroxyl -2- pyridone 3 (3a-3e), preparation
Technique is referring to attached drawing 1, comprising the following steps:
1) title disubstituted-4-hydroxy -2- pyridinone substrate (1a-1e), cuprous salt catalyst and potassium tert-butoxide are in Schleck
In bottle；Carbon dioxide is vacuumized and be passed through by Schleck bottles, makes Schleck bottles to be full of carbon dioxide gas；It is then injected into solvent
Anhydrous n,N-Dimethylformamide is placed in 100-120 DEG C of oil bath to Schleck bottles, reacts 24-36h；Wherein, 4- hydroxyl
Base -2- pyridone, potassium tert-butoxide, cuprous salt catalysts and solvents amount ratio be 1mmol:1.5mmol:0.1mmol:5mL；
2) hydrochloric acid acidification after the reaction was completed, is added, then extraction crosses silicagel column, obtains pure -4 hydroxyl of intermediate 3- carboxyl
Base -2- pyridine compounds 2 (2a-2e), recycling yield reach 84%；
3) -4 hydroxyl -2- pyridine compounds 2 (2a-2e) of 3- carboxyl and 2- methylamino pyridine obtained step 2)
And ethyl alcohol is added in container, and toluene is added, and stirs 10-30min, and 1- (3- dimethylamino-propyl) -3- ethyl carbon two is added
Inferior amine salt hydrochlorate reacts 16-24h in 50-70 DEG C of oil bath, is transferred in 100mL pear shape bottle, and ethyl alcohol (10mL) washing is added and burns
Bottle, is removed under reduced pressure solvent toluene, column chromatography for separation obtains 3 (3a- of final compound 3- Ethyl formate -4- hydroxyl -2- pyridone
3e), wherein compound 2 (2a-2e), 2- methylamino pyridine, ethyl alcohol, 1- (3- dimethylamino-propyl) -3- ethyl carbodiimide salt
The amount ratio of hydrochlorate and solvent toluene is 1mmol:1.2mmol:3mmol:1.2mmol:30mL.
1 structural formula of compound is as follows:
In R1Respectively hydrogen, methyl, hydrogen, hydrogen, hydrogen, R2 are respectively methyl, methyl, ethyl, propyl, isopropyl, specifically
Structural formula such as 1a-1e:
The advantages of the present invention:
The preparation method is simple, and cost of material is low, easily transports, is easy to industrial amplification production；This method expands titanium dioxide
The chemical reaction type that carbon can occur, the recycling for having carried out carbon dioxide recycle, and on the one hand protect environment, on the other hand
So that carbon dioxide become one kind can be with the regenerated energy.A kind of new 3- Ethyl formate -4- hydroxyl -2- pyridine is provided simultaneously
The synthetic route of ketone, so that preparation method is simpler, cost is cheaper.
Detailed description of the invention:
Fig. 1 is the process route map using carbon dioxide production 3- Ethyl formate -4- hydroxyl -2- pyridone 3a.
Specific embodiment
Embodiment 1:
A kind of process using carbon dioxide production 3- Ethyl formate -4- hydroxyl -2- pyridone 3a, preparation process is such as
Shown in Fig. 1, comprising the following steps:
1) 1mmol4- hydroxyl -2- pyridine compounds 1a, 1.5mmol potassium tert-butoxide and 0.1mmol cuprous iodide are weighed
In Schleck bottles, Schlenk bottles are vacuumized, is passed through carbon dioxide (balloon), the anhydrous N of 5mL, N- dimethyl formyl is added
Amine is heated to 100 DEG C and stirs 24 hours.
2) it after the completion of being stirred to react, is cooled to room temperature, is added in the water of 30mL, hydrochloric acid acidification is added and adjusts pH to 1, acetic acid
Ethyl ester extracts (5*20mL), and anhydrous magnesium sulfate dries, filters, and crosses silica gel column chromatography separation (ethyl acetate: petroleum ether=3:1)；
Pure intermediate product 3- carboxyl -4- hydroxyl -2- pyridine compounds 2a is obtained, weighs, is calculated back according to the molar ratio of 1a
Receive yield 84%.
3) 1mmol3- carboxyl -4- hydroxyl -2- pyridine compounds 2a is weighed in a round bottom flask, 1.2mmol2- first ammonia
30mL toluene is added in yl pyridines and 3mmol ethyl alcohol, and 1- (3- dimethylamino-propyl) -3- ethyl-carbodiimide hydrochloride is added,
It is heated to 50 DEG C and stirs 16h.It after having reacted, is cooled to room temperature, is transferred in 100mL pear shape bottle, 10mL ethanol washing is added
Solvent toluene is removed under reduced pressure in flask, and column chromatography for separation obtains final compound 3- Ethyl formate -4- hydroxyl -2- pyridone 3a,
Weighing calculates recycling yield 77% according to the molar ratio of 2a.Referring to Fig. 1.
Embodiment 2:
A kind of process using carbon dioxide production 3- Ethyl formate -4- hydroxyl -2- pyridone 3b, preparation process packet
Include following steps:
1) 1mmol4- hydroxyl -2- pyridine compounds 1b, 1.5mmol potassium tert-butoxide and 0.1mmol cuprous iodide are weighed
In Schleck bottles, Schlenk bottles are vacuumized, is passed through carbon dioxide (balloon), the anhydrous N of 5mL, N- dimethyl formyl is added
Amine is heated to 100 DEG C and stirs 24 hours.
2) it after the completion of being stirred to react, is cooled to room temperature, is added in the water of 30mL, adjust pH to 1, ethyl acetate extracts (5*
20mL), anhydrous magnesium sulfate dries, filters, column chromatography for separation (ethyl acetate: petroleum ether=3:1)；Obtain pure intermediate product
3- carboxyl -4- hydroxyl -2- pyridine compounds 2b, weighing calculate recycling yield 81% according to the molar ratio of 1b.
3) 1mmol3- carboxyl -4- hydroxyl -2- pyridine compounds 2b is weighed in a round bottom flask, 1.2mmol2- first ammonia
30mL toluene is added in yl pyridines and 3mmol ethyl alcohol, and 1- (3- dimethylamino-propyl) -3- ethyl-carbodiimide hydrochloride is added,
It is heated to 50 DEG C and stirs 16h.It after having reacted, is cooled to room temperature, is transferred in 100mL pear shape bottle, 10mL ethyl alcohol alcohol is added and washes
Flask is washed, solvent is removed under reduced pressure, column chromatography for separation obtains final compound 3b, weighing, calculates recycling according to the molar ratio of 2b and produces
Rate 75%.Referring to Fig. 1.
Embodiment 3:
A kind of process using carbon dioxide production 3- Ethyl formate -4- hydroxyl -2- pyridone 3c, preparation process packet
Include following steps:
1) 1mmol4- hydroxyl -2- pyridine compounds 1c, 1.5mmol potassium tert-butoxide and 0.1mmol cuprous iodide are weighed
In Schleck bottles, Schlenk bottles are vacuumized, is passed through carbon dioxide (balloon), the anhydrous N of 5mL, N- dimethyl formyl is added
Amine is heated to 100 DEG C and stirs 24 hours.
2) it after the completion of stirring, is cooled to room temperature, is added in the water of 30mL, adjust pH to 1, ethyl acetate extracts (5*
20mL), anhydrous magnesium sulfate dries, filters, column chromatography for separation (ethyl acetate: petroleum ether=3:1)；Obtain pure intermediate product
3- carboxyl -4- hydroxyl -2- pyridine compounds 2c, weighing calculate recycling yield 77% according to the molar ratio of 1c.
3) 1mmol3- carboxyl -4- hydroxyl -2- pyridine compounds 2c is weighed in a round bottom flask, 1.2mmol2- first ammonia
30mL toluene is added in yl pyridines and 3mmol ethyl alcohol, and 1- (3- dimethylamino-propyl) -3- ethyl-carbodiimide hydrochloride is added,
It is heated to 50 DEG C and stirs 16h.It after having reacted, is cooled to room temperature, is transferred in 100mL pear shape bottle, 10mL ethyl alcohol alcohol is added and washes
Flask is washed, solvent is removed under reduced pressure, column chromatography for separation obtains compound 3c.Weighing calculates recycling yield according to the molar ratio of 2c
73%.Referring to Fig. 1.
Embodiment 4:
A kind of process using carbon dioxide production 3- Ethyl formate -4- hydroxyl -2- pyridone 3d, preparation process packet
Include following steps:
1) 1mmol4- hydroxyl -2- pyridine compounds 1d, 1.5mmol potassium tert-butoxide and 0.1mmol cuprous iodide are weighed
In Schleck bottles, Schlenk bottles are vacuumized, is passed through carbon dioxide (balloon), the anhydrous N of 5mL, N- dimethyl formyl is added
Amine is heated to 100 DEG C and stirs 24 hours.
2) it after the completion of stirring, is cooled to room temperature, is added in the water of 30mL, adjust pH to 1, ethyl acetate extracts (5*
20mL), anhydrous magnesium sulfate dries, filters, column chromatography for separation (ethyl acetate: petroleum ether=3:1)；Obtain pure intermediate product
3- carboxyl -4- hydroxyl -2- pyridine compounds 2d, weighing calculate recycling yield 77% according to the molar ratio of 1d.
3) 1mmol3- carboxyl -4- hydroxyl -2- pyridine compounds 2d is weighed in a round bottom flask, 1.2mmol2- first ammonia
30mL toluene is added in yl pyridines and 3mmol ethyl alcohol, and 1- (3- dimethylamino-propyl) -3- ethyl-carbodiimide hydrochloride is added,
It is heated to 50 DEG C and stirs 16h.It after having reacted, is cooled to room temperature, is transferred in 100mL pear shape bottle, 10mL ethyl alcohol alcohol is added and washes
Flask is washed, solvent is removed under reduced pressure, column chromatography for separation obtains compound 3d.Weighing calculates recycling yield according to the molar ratio of 2d
79%.Referring to Fig. 1.
Embodiment 5:
A kind of process using carbon dioxide production 3- Ethyl formate -4- hydroxyl -2- pyridone 3e, preparation process packet
Include following steps:
1) 1mmol4- hydroxyl -2- pyridine compounds 1e, 1.5mmol potassium tert-butoxide and 0.1mmol cuprous iodide are weighed
In Schleck bottles, Schlenk bottles are vacuumized, is passed through carbon dioxide (balloon), the anhydrous N of 5mL, N- dimethyl formyl is added
Amine is heated to 100 DEG C and stirs 24 hours.
2) it after the completion of stirring, is cooled to room temperature, is added in the water of 30mL, adjust pH to 1, ethyl acetate extracts (5*
20mL), anhydrous magnesium sulfate dries, filters, column chromatography for separation (ethyl acetate: petroleum ether=3:1)；Obtain pure intermediate product
3- carboxyl -4- hydroxyl -2- pyridine compounds 2e, weighing calculate recycling yield 81% according to the molar ratio of 1e.
3) 1mmol3- carboxyl -4- hydroxyl -2- pyridine compounds 2e is weighed in a round bottom flask, 1.2mmol2- first ammonia
30mL toluene is added in yl pyridines and 3mmol ethyl alcohol, and 1- (3- dimethylamino-propyl) -3- ethyl-carbodiimide hydrochloride is added,
It is heated to 50 DEG C and stirs 16h.It after having reacted, is cooled to room temperature, is transferred in 100mL pear shape bottle, 10mL ethyl alcohol alcohol is added and washes
Flask is washed, solvent is removed under reduced pressure, column chromatography for separation obtains compound 3b.Weighing calculates recycling yield according to the molar ratio of 2e
79%.Referring to Fig. 1.
Embodiment 6:
A kind of process using carbon dioxide production 3- Ethyl formate -4- hydroxyl -2- pyridone 3a, except step 1)
Heating temperature is changed to other than 110 DEG C, remaining preparation process is the same as embodiment 1.
Embodiment 7:
A kind of process using carbon dioxide production 3- Ethyl formate -4- hydroxyl -2- pyridone 3b, except step 1)
Heating temperature is changed to other than 110 DEG C, remaining preparation process is the same as embodiment 2.
Embodiment 8:
A kind of process using carbon dioxide production 3- Ethyl formate -4- hydroxyl -2- pyridone 3c, except step 1)
Heating temperature is changed to other than 110 DEG C, remaining preparation process is the same as embodiment 3.
Embodiment 9:
A kind of process using carbon dioxide production 3- Ethyl formate -4- hydroxyl -2- pyridone 3d, except step 1)
Heating temperature is changed to other than 110 DEG C, remaining preparation process is the same as embodiment 4.
Embodiment 10:
A kind of process using carbon dioxide production 3- Ethyl formate -4- hydroxyl -2- pyridone 3e, except step 1)
Heating temperature is changed to other than 110 DEG C, remaining preparation process is the same as embodiment 5.
Embodiment 11:
A kind of process using carbon dioxide production 3- Ethyl formate -4- hydroxyl -2- pyridone 3a, except step 1)
Heating temperature is changed to other than 120 DEG C, remaining preparation process is the same as embodiment 1.
Embodiment 12:
A kind of process using carbon dioxide production 3- Ethyl formate -4- hydroxyl -2- pyridone 3b, except step 1)
Heating temperature is changed to other than 120 DEG C, remaining preparation process is the same as embodiment 2.
Embodiment 13:
A kind of process using carbon dioxide production 3- Ethyl formate -4- hydroxyl -2- pyridone 3c, except step 1)
Heating temperature is changed to other than 120 DEG C, remaining preparation process is the same as embodiment 3.
Embodiment 14:
A kind of process using carbon dioxide production 3- Ethyl formate -4- hydroxyl -2- pyridone 3d, except step 1)
Heating temperature is changed to other than 120 DEG C, remaining preparation process is the same as embodiment 4.
Embodiment 15:
A kind of process using carbon dioxide production 3- Ethyl formate -4- hydroxyl -2- pyridone 3e, except step 1)
Heating temperature is changed to other than 120 DEG C, remaining preparation process is the same as embodiment 5.
Claims (2)
1. a kind of process using carbon dioxide production 3- Ethyl formate -4- hydroxyl -2- pyridone 3 (3a-3e), step is such as
Under:
1) title disubstituted-4-hydroxy -2- pyridinone substrate (1a-1e), cuprous salt catalyst and potassium tert-butoxide are in Schleck bottles；
Carbon dioxide is vacuumized and be passed through by Schleck bottles, makes Schleck bottles to be full of carbon dioxide gas；It is anhydrous to be then injected into solvent
N,N-Dimethylformamide is placed in 100-120 DEG C of oil bath to Schleck bottles, reacts 24-36h；Wherein, 4- hydroxyl -2-
Pyridone, potassium tert-butoxide, cuprous salt catalysts and solvents amount ratio be 1mmol:1.5mmol:0.1mmol:5mL；
2) hydrochloric acid acidification after the reaction was completed, is added, then extraction crosses silicagel column, obtains pure -4 hydroxyl -2- of intermediate 3- carboxyl
Pyridine compounds 2 (2a-2e), recycling yield reach 84%；
3) -4 hydroxyl -2- pyridine compounds 2 (2a-2e) of 3- carboxyl and 2- methylamino pyridine that obtain step 2) and
Reactant ethyl alcohol is added in container, and solvent toluene is added, and stirs 10-30min, and 1- (3- dimethylamino-propyl) -3- second is added
Base carbodiimide hydrochloride reacts 16-24h in 50-70 DEG C of oil bath, is transferred in 100mL pear shape bottle, and ethanol washing is added and burns
Bottle, is removed under reduced pressure toluene, and column chromatography for separation obtains final compound 3- Ethyl formate -4- hydroxyl -2- pyridone 3 (3a-3e),
Wherein compound 2 (2a-2e), 2- methylamino pyridine, ethyl alcohol, 1- (3- dimethylamino-propyl) -3- ethyl-carbodiimide hydrochloride
Amount ratio with solvent toluene is 1mmol:1.2mmol:3mmol:1.2mmol:30mL.
2. the technique side according to claim 1 using carbon dioxide production 3- Ethyl formate -4- hydroxyl -2- pyridone
Method, which is characterized in that the cuprous salt catalyst is cuprous iodide.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1655677A (en) * | 2002-05-24 | 2005-08-17 | 住友化学株式会社 | Use of ester compound for controlling harmful arthropod |
| CN109452280A (en) * | 2018-11-15 | 2019-03-12 | 南开大学 | A kind of process using carbon dioxide production insecticide |
-
2019
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1655677A (en) * | 2002-05-24 | 2005-08-17 | 住友化学株式会社 | Use of ester compound for controlling harmful arthropod |
| CN109452280A (en) * | 2018-11-15 | 2019-03-12 | 南开大学 | A kind of process using carbon dioxide production insecticide |
Non-Patent Citations (1)
| Title |
|---|
| WILLIAM T. MCELROY等: "Siloxane-Based Cross-Coupling of Bromopyridine Derivatives: Studies for the Synthesis of Streptonigrin and Lavendamycin", 《ORGANIC LETTERS》 * |
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