CN106632190B - 7-(diethylamino) -2- oxo -2H- chromene -3- carboxylic acid preparation method - Google Patents
7-(diethylamino) -2- oxo -2H- chromene -3- carboxylic acid preparation method Download PDFInfo
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- CN106632190B CN106632190B CN201710003448.2A CN201710003448A CN106632190B CN 106632190 B CN106632190 B CN 106632190B CN 201710003448 A CN201710003448 A CN 201710003448A CN 106632190 B CN106632190 B CN 106632190B
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- Prior art keywords
- chromene
- oxo
- carboxylic acid
- diethylamino
- lignocaine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
A kind of 7-(diethylamino provided by the invention) -2- oxo -2H- chromene -3- carboxylic acid preparation method, step includes: that 7- (lignocaine) -2- oxo -2H- chromene -3- formaldehyde dissolves in methyl alcohol, the sodium hypochlorite that concentration is 8-10% is added, it is stirred at room temperature 5-10 minutes, it is diluted with deionized water, product is extracted with chloroform again, organic phase is evaporated, the solid of yellow is obtained.The method of the present invention synthesis process is simple, at low cost, environmentally protective, the time is short, yield is up to 82%.
Description
Technical field
The present invention relates to the preparation method of Coumarins carboxylic acid compound, specifically a kind of 7- (diethylamino) -2- oxygen
The preparation method of generation -2H- chromene -3- carboxylic acid.
Background technique
Green, sustainable synthesis is the trend of modern organic chemistry development, is developed " green synthetic method " and quick
Obtain the main target that target compound is current organic synthesis.In fact, the preparation of carboxylic acid compound is in Coordinative Chemistry, life
Object chemistry, pharmacology, material science etc. occupy an important position, and many natural products are carboxylic acid compounds.For example, caffeic acid
It is antiviral with antibacterial, central excitation, removing toxic substances, the effects of blood coagulation.So developing, one kind is environmentally protective, preparation time is short, produces
The synthetic method of the high carboxylic acid compound of rate is necessary.And carboxylic acid compound is currently prepared, it generally requires more
Step synthesis, and many times need to heat, add catalyst that can just be prepared, the present invention is directed to this case, using secondary chlorine
Sour sodium oxidation aldehyde radical prepares corresponding carboxylic acid compound, and the preparation method can under mild conditions (room temperature, normal pressure)
It carries out.
Summary of the invention
The object of the present invention is to provide a kind of preparation method of 7- (diethylamino) -2- oxo -2H- chromene -3- carboxylic acid,
This method answers that inexpensive, environmentally protective, quick, yield is high.
A kind of preparation method of 7- (diethylamino) -2- oxo -2H- chromene -3- carboxylic acid provided by the invention, step packet
It includes: in methyl alcohol by the dissolution of 7- (lignocaine) -2- oxo -2H- chromene -3- formaldehyde, the hypochlorous acid that concentration is 8-10% is added
The molar ratio of sodium, 7- (the lignocaine) -2- oxo -2H- chromene -3- formaldehyde and sodium hypochlorite is 1: 10-20；At room temperature
Stirring 5-10 minutes, is diluted with deionized water, then extracts product with chloroform, and organic phase is evaporated, the solid of yellow is obtained.
Reaction equation:
Synthesis condition in above-mentioned steps is further preferred are as follows:
The molar ratio of 7- (the lignocaine) -2- oxo -2H- chromene -3- formaldehyde and sodium hypochlorite is 1: 15.
The sodium hypochlorite concentration is 10%.
The reaction time at room temperature is 5 minutes.
Compared with prior art, the invention has the advantages that and effect: 7- (diethylamino) -2- oxo -2H- color
Alkene -3- carboxylic acid synthesis process is at low cost, environmentally protective, the time is short, no coupling product, yield are up to 82%.
Detailed description of the invention:
The nucleus magnetic hydrogen spectrum figure of 7- (diethylamino) -2- oxo -2H- chromene -3- carboxylic acid prepared by Fig. 1 embodiment 1
The nucleus magnetic hydrogen spectrum figure of 7- (diethylamino) -2- oxo -2H- chromene -3- carboxylic acid prepared by Fig. 2 embodiment 1
The mass spectrogram of 7- (diethylamino) -2- oxo -2H- chromene -3- carboxylic acid prepared by Fig. 3 embodiment 1
Specific embodiment:
Embodiment 1
7- (lignocaine) -2- oxo -2H- chromene -3- formaldehyde (0.2453g, 1mmol) is dissolved in 10ml methanol,
The sodium hypochlorite 10.05mL (15mmol) that concentration is 10% is added, is stirred at room temperature 5 minutes, it is dilute with the deionized water of 10mL
It releases, and extracts product with the chloroform of 30mL, chloroform organic phase is evaporated to obtain 7- (diethylamino) -2- oxo -
2H- chromene -3- carboxylic acid 0.2142g (yield 82%).1H NMR(300MHz,25℃,CDCl3):δ12.29(s,1H),8.57
(s, 1H), 7.39-7.36 (d, J=9.0Hz, 1H), 6.66-6.62 (m, J=12.0Hz, 1H), 6.46 (s, 1H), 3.46-
3.39 (m, J=21.0 Hz, 4H), 1.22-1.17 (t, J=15.0Hz, 6H) (Fig. 1)；13C NMR(75MHz,CDCl3):δ
166.50,165.41, 159.00,154.74,151.20,132.92,111.91,109.50,106.44,97.78,46.33,
(13.36 Fig. 2)；ESI-MS(m/z): 262.00,[M+H]+and 284.00,[M+Na]+(Fig. 3).
Claims (1)
1. a kind of preparation method of 7- (diethylamino) -2- oxo -2H- chromene -3- carboxylic acid, which is characterized in that step includes:
In methyl alcohol by the dissolution of 7- (lignocaine) -2- oxo -2H- chromene -3- formaldehyde, the sodium hypochlorite that concentration is 10% is added,
It stirs 5 minutes, is diluted with deionized water at room temperature, then extract product with chloroform, organic phase is evaporated, consolidating for yellow is obtained
Body；The molar ratio of 7- (the lignocaine) -2- oxo -2H- chromene -3- formaldehyde and sodium hypochlorite is 1: 15.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710003448.2A CN106632190B (en) | 2017-01-04 | 2017-01-04 | 7-(diethylamino) -2- oxo -2H- chromene -3- carboxylic acid preparation method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710003448.2A CN106632190B (en) | 2017-01-04 | 2017-01-04 | 7-(diethylamino) -2- oxo -2H- chromene -3- carboxylic acid preparation method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106632190A CN106632190A (en) | 2017-05-10 |
| CN106632190B true CN106632190B (en) | 2018-12-07 |
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| CN201710003448.2A Expired - Fee Related CN106632190B (en) | 2017-01-04 | 2017-01-04 | 7-(diethylamino) -2- oxo -2H- chromene -3- carboxylic acid preparation method |
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Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006023821A2 (en) * | 2004-08-20 | 2006-03-02 | The Trustees Of Columbia University In The City Of New York | Ligands for aldoketoreductases |
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2017
- 2017-01-04 CN CN201710003448.2A patent/CN106632190B/en not_active Expired - Fee Related
Non-Patent Citations (2)
| Title |
|---|
| The Synthesis and Light Absorption Behaviour of Novel Coumarin Chromophores;Kyoung Lyong An et al.;《Journal of the Korean Chemical Society》;20140630;第58卷(第3期);297-302 * |
| 糠醛氧化制糠酸反应条件研究;杨光瑞;《河南师范大学，硕士学位论文》;20061117;第7页第2段 * |
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| CN106632190A (en) | 2017-05-10 |
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Granted publication date: 20181207 Termination date: 20220104 |