CN106632016A - Synthesis method of 2-acetamido-5-bromopyridine - Google Patents
Synthesis method of 2-acetamido-5-bromopyridine Download PDFInfo
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- CN106632016A CN106632016A CN201611016017.1A CN201611016017A CN106632016A CN 106632016 A CN106632016 A CN 106632016A CN 201611016017 A CN201611016017 A CN 201611016017A CN 106632016 A CN106632016 A CN 106632016A
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- bromopyridines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a synthesis method of 2-acetamido-5-bromopyridine. 2-amino-5-bromopyridine and acetic anhydride are used as raw materials; the mol ratio of the 2-amino-5-bromopyridine to the acetic anhydride is 1: (0.85 to 3.6); in a proper solvent, the continuous reaction is performed at 45 to 115 DEG C to generate a coarse product of 2-acetamido-5-bromopyridine; after the purification, a pure product of the 2-acetamido-5-bromopyridine is obtained. The method has the advantages that the raw materials can be easily obtained; the price is reasonable; meanwhile, heavy metal and corrosive gas are not used in the preparation reaction; the reaction is mild; no special requirements exist on reaction equipment; the production can be performed by ordinary anti-corrosion equipment; in addition, the reaction conditions of the method are proper; no pollution can be caused on the environment.
Description
（One）Technical field
The invention belongs to organic synthesis field, and in particular to a kind of synthetic method of 2- acetylaminohydroxyphenylarsonic acids 5- bromopyridines.
（Two）Background technology
In May, 2014 No. 7 discloses a kind of novel synthesis of 2- amino -4- bromopyridines, and it is comprised the following steps：
(1) amino of the picoline of 2- amino 4 carries out acetyl protection；
(2) and then carry out oxidation and obtain 2- acetylaminohydroxyphenylarsonic acid 4- pyridine carboxylic acids；
(3) dppa resets and obtains 4 amino boc-2- acetylamino pyridines；
(4) hydrobromic acid backflow obtains the bromopyridine of 2 amino 4.
2- acetylaminohydroxyphenylarsonic acid 5- bromopyridines, as a kind of bromopyridine analog derivative, are the important intermediates of organic synthesis, mainly
For medicine intermediate, organic synthesis, organic solvent, the aspects such as DYE PRODUCTION, pesticide producing and spices are also apply be applicable to.
The preparation of existing bromopyridine is suffered from the drawback that：
（1）Accessory substance is more, causes the color and luster of product deeper, it is difficult to refined purification.Although repeatedly can again be tied with organic solvent
Crystalline substance, but quality still cannot meet high request, and also repeated crystallization causes product yield low, and cost increases, cumbersome；
(2) chemical reduction method for being used is all extremely serious to the corrosion of equipment and the pollution of environment, at present Limit exploitation；
(3) raw material sources are limited, expensive, and operation is more bothered.
The problems referred to above are required to improve.
（Three）The content of the invention
The present invention is in order to make up the deficiencies in the prior art, there is provided the synthetic method of 2- acetylaminohydroxyphenylarsonic acid 5- bromopyridines, the synthesis side
Method is simple to operate, yield is high, it is adaptable to laboratory and industrialized production.
The present invention is achieved through the following technical solutions：
A kind of synthetic method of 2- acetylaminohydroxyphenylarsonic acids 5- bromopyridines, it is characterized in that：Comprise the following steps：
With 2- amino -5- bromopyridines, acetic anhydride as raw material, 2- amino -5- bromopyridines, the ratio of the amount of both acetic anhydrides material is 1:
0.85-3.6, in appropriate solvent, in 45-115 DEG C of successive reaction 2- acetylaminohydroxyphenylarsonic acid 5- bromopyridine crude products is generated, and Jing is carried
2- acetylaminohydroxyphenylarsonic acid 5- bromopyridine sterlings are obtained after pure.
The synthetic method of the 2- acetylaminohydroxyphenylarsonic acid 5- bromopyridines of the present invention, it is characterised in that：Solvent is isopropanol, n-hexane,
Water, ethyl acetate, ethanol, acetonitrile, the tert-butyl alcohol, acetic acid, dichloromethane, one or two in chloroform.
The synthetic method of the 2- acetylaminohydroxyphenylarsonic acid 5- bromopyridines of the present invention, it is characterised in that：The inventory of reactant and solvent
For：m（2- amino -5- bromopyridines）：m（Solvent）=1:1.1-12, it is more than weight ratio.
The synthetic method of the 2- acetylaminohydroxyphenylarsonic acid 5- bromopyridines of the present invention, it is characterised in that：Purification step is addition extractant
Extraction, rotary evaporation concentration, recrystallization.
The synthetic method of the 2- acetylaminohydroxyphenylarsonic acid 5- bromopyridines of the present invention, it is characterised in that：The solvent of recrystallization is described heavy
Recrystallisation solvent be ethyl acetate/n-hexane mixed solvent, ethyl acetate：N-hexane=1:4, it is more than volume ratio.
The synthetic method of the 2- acetylaminohydroxyphenylarsonic acid 5- bromopyridines of the present invention, it is characterised in that：In 45-115 DEG C of successive reaction 5-
16 hours.
The synthesis technique and synthesis step of 2- acetylaminohydroxyphenylarsonic acids 5- bromopyridines of the present invention is as follows：
Beneficial effects of the present invention：2- acetylaminohydroxyphenylarsonic acid 5- bromopyridines are prepared using the present invention, reaction condition is gentle, it is easy to operate,
And product quality is stable, purity is high.
（Four）Specific embodiment
Embodiment 1：
2- amino -5- bromopyridines are added in 50 milliliters of single necked round bottom flask（1.73g, 10mmol）, acetic anhydride（1.02g,
10mmol）With tert-butyl alcohol 10ml, magnetic stirring apparatus is started, stirring reaction 12 hours at 75 DEG C of the mixture in reaction bulb.TLC
Determine that the reaction of raw material 2- amino -5- bromopyridines is complete with GC detections, add water in reactant liquor, then by reactant liquor suction filtration, filter cake
Use ethyl acetate：N-hexane=1:4 are recrystallized to give net product 2- acetylaminohydroxyphenylarsonic acid 5- bromopyridines, and filtrate is extracted with ethyl acetate,
Revolving removes extractant, obtains crude product, then uses ethyl acetate：N-hexane=1:4 are recrystallized to give net product 2- acetylaminohydroxyphenylarsonic acids
5- bromopyridines, after being dried, calculated yield 61.42%, purity 98.71%（HPLC）, nuclear magnetic resonance spectroscopy： 1HNMR (400Hz, it is deuterated
DMSO)δ:10.656 (s, 1H), 8.405 (d, 1H), 8.052 (d, 1H), 7.982 (dd, 1H), 2.094 (s, 3H).
Embodiment 2：
2- amino -5- bromopyridines are added in 50 milliliters of single necked round bottom flask（1.73g, 10mmol）, acetic anhydride（1.53g,
15mmol）With ethanol 12ml, magnetic stirring apparatus is started, stirring reaction 12 hours at 75 DEG C of the mixture in reaction bulb.TLC and
GC detections determine that the reaction of raw material 2- amino -5- bromopyridines is complete, add water in reactant liquor, and then by reactant liquor suction filtration, filter cake is used
Ethyl acetate：N-hexane=1:4 are recrystallized to give net product 2- acetylaminohydroxyphenylarsonic acid 5- bromopyridines, and filtrate is extracted with ethyl acetate, rotation
Extractant is evaporated off, crude product is obtained, then uses ethyl acetate：N-hexane=1:4 are recrystallized to give net product 2- acetylaminohydroxyphenylarsonic acid 5-
Bromopyridine, after being dried, calculated yield 68.20%, purity 98.63%（HPLC）.
Embodiment 3：
2- amino -5- bromopyridines are added in 500 milliliters of single necked round bottom flask（17.30g, 100mmol）, acetic anhydride
（15.30g, 150mmol）With ethanol 160ml, magnetic stirring apparatus is started, the stirring reaction 11 at 75 DEG C of the mixture in reaction bulb
Hour.TLC and GC detections determine that the reaction of raw material 2- amino -5- bromopyridines is complete, add water in reactant liquor, then take out reactant liquor
Filter, filter cake ethyl acetate：N-hexane=1:4 are recrystallized to give net product 2- acetylaminohydroxyphenylarsonic acid 5- bromopyridines, and filtrate uses acetic acid second
Ester is extracted, and revolving removes extractant, obtains crude product, then uses ethyl acetate：N-hexane=1:4 are recrystallized to give net product 2- second
Acylamino- -5- bromopyridines, after being dried, calculated yield 78.49%, the % of purity 99.00（HPLC）.
Embodiment 4：
2- amino -5- bromopyridines are added in 500 milliliters of single necked round bottom flask（17.30g, 100mmol）, acetic anhydride
（18.36g, 180mmol）With ethyl acetate 160ml, magnetic stirring apparatus is started, the mixture in reaction bulb is stirred instead at 80 DEG C
Answer 10 hours.TLC and GC detections determine that the reaction of raw material 2- amino -5- bromopyridines is complete, add water in reactant liquor, then will reaction
Liquid suction filtration, filter cake ethyl acetate：N-hexane=1:4 are recrystallized to give net product 2- acetylaminohydroxyphenylarsonic acid 5- bromopyridines, filtrate second
Acetoacetic ester is extracted, and revolving removes extractant, obtains crude product, then uses ethyl acetate：N-hexane=1:4 are recrystallized to give net product
2- acetylaminohydroxyphenylarsonic acid 5- bromopyridines, after being dried, calculated yield 80.60%, the % of purity 99.36（HPLC）.
Embodiment 5：
2- amino -5- bromopyridines are added in 1000 milliliters of single necked round bottom flask（34.60g, 200mmol）, acetic anhydride
（40.80g, 400mmol）With ethanol 520ml, magnetic stirring apparatus is started, the stirring reaction 10 at 80 DEG C of the mixture in reaction bulb
Hour.TLC and GC detections determine that the reaction of raw material 2- amino -5- bromopyridines is complete, add water in reactant liquor, then take out reactant liquor
Filter, filter cake ethyl acetate：N-hexane=1:4 are recrystallized to give net product 2- acetylaminohydroxyphenylarsonic acid 5- bromopyridines, and filtrate uses acetic acid second
Ester is extracted, and revolving removes extractant, obtains crude product, then uses ethyl acetate：N-hexane=1:4 are recrystallized to give net product 2- second
Acylamino- -5- bromopyridines, after being dried, calculated yield 82.47%, the % of purity 98.52（HPLC）.
Embodiment 6：
2- amino -5- bromopyridines are added in 1000 milliliters of single necked round bottom flask（34.60g, 200mmol）, acetic anhydride
（44.88g, 440mmol）With acetonitrile 520ml, magnetic stirring apparatus is started, the stirring reaction 10 at 80 DEG C of the mixture in reaction bulb
Hour.TLC and GC detections determine that the reaction of raw material 2- amino -5- bromopyridines is complete, add water in reactant liquor, then take out reactant liquor
Filter, filter cake ethyl acetate：N-hexane=1:4 are recrystallized to give net product 2- acetylaminohydroxyphenylarsonic acid 5- bromopyridines, and filtrate uses acetic acid second
Ester is extracted, and revolving removes extractant, obtains crude product, then uses ethyl acetate：N-hexane=1:4 are recrystallized to give net product 2- second
Acylamino- -5- bromopyridines, after being dried, calculated yield 84.29%, the % of purity 98.91（HPLC）.
Embodiment 7：
2- amino -5- bromopyridines are added in 2000 milliliters of single necked round bottom flask（86.50g, 500mmol）, acetic anhydride
（153g, 1500mmol）With acetic acid 850ml, magnetic stirring apparatus is started, the stirring reaction 9 at 100 DEG C of the mixture in reaction bulb
Hour.TLC and GC detections determine that the reaction of raw material 2- amino -5- bromopyridines is complete, add water in reactant liquor, then take out reactant liquor
Filter, filter cake ethyl acetate：N-hexane=1:4 are recrystallized to give net product 2- acetylaminohydroxyphenylarsonic acid 5- bromopyridines, and filtrate uses acetic acid second
Ester is extracted, and revolving removes extractant, obtains crude product, then uses ethyl acetate：N-hexane=1:4 are recrystallized to give net product 2- second
Acylamino- -5- bromopyridines, after being dried, calculated yield 75.40%, the % of purity 99.68（HPLC）.
Embodiment 8：
2- amino -5- bromopyridines are added in 2000 milliliters of single necked round bottom flask（86.50g, 500mmol）, acetic anhydride
（183.60g, 1800mmol）With acetic acid and the common 900ml of acetonitrile（Wherein acetic acid 300ml）, magnetic stirring apparatus is started, in reaction bulb
Mixture at 100 DEG C stirring reaction 9 hours.TLC and GC detections determine that the reaction of raw material 2- amino -5- bromopyridines is complete, to
Add water in reactant liquor, then by reactant liquor suction filtration, filter cake ethyl acetate：N-hexane=1:4 are recrystallized to give net product 2- acetyl
Amino -5- bromopyridines, filtrate is extracted with ethyl acetate, and revolving removes extractant, obtains crude product, then uses ethyl acetate：Just oneself
Alkane=1:4 are recrystallized to give net product 2- acetylaminohydroxyphenylarsonic acid 5- bromopyridines, after being dried, calculated yield 63.72%, and the % of purity 98.48
（HPLC）.
Embodiment 9：
2- amino -5- bromopyridines are added in 2000 milliliters of single necked round bottom flask（500mmol）, acetic anhydride（600mmol）With
Acetic acid and the common 500ml of acetonitrile（Wherein acetic acid 200ml）, magnetic stirring apparatus is started, the mixture in reaction bulb is stirred at 45 DEG C
Reaction 16 hours.TLC and GC detections determine that the reaction of raw material 2- amino -5- bromopyridines is complete, add water in reactant liquor, then will be anti-
Answer liquid suction filtration, filter cake ethyl acetate：N-hexane=1:4 are recrystallized to give net product 2- acetylaminohydroxyphenylarsonic acid 5- bromopyridines, and filtrate is used
Ethyl acetate is extracted, and revolving removes extractant, obtains crude product, then uses ethyl acetate：N-hexane=1:4 are recrystallized to give pure product
Product 2- acetylaminohydroxyphenylarsonic acid 5- bromopyridines, after being dried, calculated yield 62.4%, the % of purity 98.1（HPLC）.
Embodiment 10：
2- amino -5- bromopyridines are added in 2000 milliliters of single necked round bottom flask（500mmol）, acetic anhydride（600mmol）With
Acetic acid 500ml, starts magnetic stirring apparatus, stirring reaction 2.5 hours at 115 DEG C of the mixture in reaction bulb.TLC and GC is detected
Determine that the reaction of raw material 2- amino -5- bromopyridines is complete, add water in reactant liquor, then by reactant liquor suction filtration, filter cake acetic acid second
Ester：N-hexane=1:4 are recrystallized to give net product 2- acetylaminohydroxyphenylarsonic acid 5- bromopyridines, and filtrate is extracted with ethyl acetate, and revolving is removed
Extractant, obtains crude product, then uses ethyl acetate：N-hexane=1:4 are recrystallized to give net product 2- acetylaminohydroxyphenylarsonic acid 5- bromopyridines,
After drying, calculated yield 68.4%, the % of purity 98.1（HPLC）.
Embodiment 11：
2- amino -5- bromopyridines are added in 2000 milliliters of single necked round bottom flask（500mmol）, acetic anhydride（600mmol）With
Ethanol 800ml, starts magnetic stirring apparatus, stirring reaction 2.5 hours at 110 DEG C of the mixture in reaction bulb.TLC and GC is detected
Determine that the reaction of raw material 2- amino -5- bromopyridines is complete, add water in reactant liquor, then by reactant liquor suction filtration, filter cake acetic acid second
Ester：N-hexane=1:4 are recrystallized to give net product 2- acetylaminohydroxyphenylarsonic acid 5- bromopyridines, and filtrate is extracted with ethyl acetate, and revolving is removed
Extractant, obtains crude product, then uses ethyl acetate：N-hexane=1:4 are recrystallized to give net product 2- acetylaminohydroxyphenylarsonic acid 5- bromopyridines,
After drying, calculated yield 81.1%, purity 98.4%（HPLC）.
Claims (6)
1. a kind of imidazo（1,2, b）The synthetic method of pyrazine -3- Ethyl formates, it is characterised in that：Comprise the following steps：
With 2- amino -5- bromopyridines, acetic anhydride as raw material, 2- amino -5- bromopyridines, the ratio of the amount of both acetic anhydrides material is 1:
0.85-3.6, in appropriate solvent, in 45-115 DEG C of successive reaction 2- acetylaminohydroxyphenylarsonic acid 5- bromopyridine crude products is generated, and Jing is carried
2- acetylaminohydroxyphenylarsonic acid 5- bromopyridine sterlings are obtained after pure.
2. the synthetic method of 2- acetylaminohydroxyphenylarsonic acids 5- bromopyridines according to claim 1, it is characterised in that：Solvent is isopropyl
Alcohol, n-hexane, water, ethyl acetate, ethanol, acetonitrile, the tert-butyl alcohol, acetic acid, dichloromethane, one or two in chloroform.
3. the synthetic method of 2- acetylaminohydroxyphenylarsonic acids 5- bromopyridines according to claim 1 and 2, it is characterised in that：Reactant with
The inventory of solvent is：m（2- amino -5- bromopyridines）：m（Solvent）=1:1.1-12, it is more than weight ratio.
4. the synthetic method of 2- acetylaminohydroxyphenylarsonic acids 5- bromopyridines according to claim 1 and 2, it is characterised in that：Purification step
To add extractant extraction, it is concentrated by evaporation, recrystallization.
5. the synthetic method of 2- acetylaminohydroxyphenylarsonic acids 5- bromopyridines according to claim 1 and 2, it is characterised in that：Recrystallization is molten
Agent be ethyl acetate/n-hexane mixed solvent, ethyl acetate：N-hexane=1:4, it is more than volume ratio.
6. the synthetic method of 2- acetylaminohydroxyphenylarsonic acids 5- bromopyridine pyridines according to claim 1 and 2, it is characterised in that：
5-16 hour of 45-115 DEG C of reaction.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115010656A (en) * | 2022-06-14 | 2022-09-06 | 苏州昊帆生物股份有限公司 | Preparation method of 5-acetyl-2-bromopyridine |
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- 2016-11-18 CN CN201611016017.1A patent/CN106632016A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115010656A (en) * | 2022-06-14 | 2022-09-06 | 苏州昊帆生物股份有限公司 | Preparation method of 5-acetyl-2-bromopyridine |
| CN115010656B (en) * | 2022-06-14 | 2024-04-26 | 苏州昊帆生物股份有限公司 | Preparation method of 5-acetyl-2-bromopyridine |
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