CN103804223A - 2-hydroxy-3-(2-hydroxy-3-ethyoxyl-N-methyl benzene) acetophenone and synthesis method thereof - Google Patents
2-hydroxy-3-(2-hydroxy-3-ethyoxyl-N-methyl benzene) acetophenone and synthesis method thereof Download PDFInfo
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- CN103804223A CN103804223A CN201410056166.5A CN201410056166A CN103804223A CN 103804223 A CN103804223 A CN 103804223A CN 201410056166 A CN201410056166 A CN 201410056166A CN 103804223 A CN103804223 A CN 103804223A
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Abstract
The invention discloses 2-hydroxy-3-(2-hydroxy-3-ethyoxyl-N-methyl benzene) acetophenone and a synthesis method thereof. The molecular formula of the 2-hydroxy-3-(2-hydroxy-3-ethyoxyl-N-methyl benzene) acetophenone is C17H18NO4, the molecular weight is 300.33, and the 2-hydroxy-3-(2-hydroxy-3-ethyoxyl-N-methyl benzene) acetophenone is of a triclinic system, and comprises P-1 space groups. The synthesis method comprises the following steps: (1) adding 1.6-1.8g of analytically pure 3-ethyoxyl salicylaldehyde and 40-42ml of absolute methanol to a three-necked flask, and heating to dissolve; (2) adding 40-42ml of absolute methanol solution into which 1.5-1.7g of analytically pure 3-amido-2-hydroxyacetophenone is dissolved to the solution obtained in the step (1) under agitation; (3) dropwise adding 1.0-1.4ml of absolute acetic acid to the solution obtained in the step (2), refluxing and agitating at 60-70 DEG C for 1.5-2.0 hours, cooling to room temperature, filtering, and washing by using an anhydrous ethanol solution, so as to obtain a red crystal product. The 2-hydroxy-3-(2-hydroxy-3-ethyoxyl-N-methyl benzene) acetophenone has the advantages of being simple in process, low in cost, easy to control chemical components, good in repeatability, high in yield and the like.
Description
Technical field
The present invention relates to a kind of 2-hydroxyl-3-(the sub-benzene methanamine of 2-hydroxyl-3-oxyethyl group) methyl phenyl ketone and synthetic method.
Background technology
In the past few decades, show that about the research of salicylic aldehyde and schiff bases they have good biological activity.And there is unique biological activity with the synthetic asymmetric schiff bases 2-hydroxyl-3-of 3-oxyethyl group salicylic aldehyde and 3-amino-2-hydroxy acetophenone (the sub-benzene methanamine of 2-hydroxyl-3-oxyethyl group) methyl phenyl ketone, can be as the effectively presoma of the medicine such as antibacterial, antitumor, functional materials of the synthetic low toxicity with application prospect of design.Just there is multiple coordination mode and itself construct title complex as part, may become a kind of good part that has, there is important potential use.
Summary of the invention
Object of the present invention is exactly to be the synthetic asymmetric schiff bases of design, utilizes water-bath synthetic technology to synthesize 2-hydroxyl-3-(the sub-benzene methanamine of 2-hydroxyl-3-oxyethyl group) methyl phenyl ketone.
The molecular formula of 2-hydroxyl-3-(the sub-benzene methanamine of the 2-hydroxyl-3-oxyethyl group) methyl phenyl ketone the present invention relates to is: C
17h
18nO
4, molecular weight is: 300.33, and triclinic(crystalline)system, P-1 spacer.
The synthetic method concrete steps of described 2-hydroxyl-3-(the sub-benzene methanamine of 2-hydroxyl-3-oxyethyl group) methyl phenyl ketone are:
(1) 1.6-1.8 gram of analytical pure 3-oxyethyl group salicylic aldehyde and 40-42 milliliter anhydrous methanol are joined in there-necked flask, be heated to dissolve.
(2) under agitation in the solution of step (1) gained, add 40-42 milliliter to be dissolved with the absolute methanol solution of 1.5-1.7 gram of analytical pure 3-amino-2-hydroxy acetophenone.
(3) drip 1.0-1.4 milliliter anhydrous acetic acid to the prepared solution of step (2), and at 60-70 ℃ of return stirring 1.5-2.0 hour; Be cooled to room temperature, filter, with ethanol solution washing, obtain red crystals shape product 2-hydroxyl-3-(the sub-benzene methanamine of 2-hydroxyl-3-oxyethyl group) methyl phenyl ketone.
The present invention has that technique is simple, with low cost, chemical composition is easy to control, reproducible and output advantages of higher.
Accompanying drawing explanation
Fig. 1 is the enforcement figure of 2-hydroxyl-3-of the present invention (the sub-benzene methanamine of 2-hydroxyl-3-oxyethyl group) methyl phenyl ketone.
Fig. 2 is the structure iron (obtaining detailed structural information by single crystal diffractometer) of 2-hydroxyl-3-of the present invention (the sub-benzene methanamine of 2-hydroxyl-3-oxyethyl group) methyl phenyl ketone.
Embodiment
Embodiment:
The molecular formula of 2-hydroxyl-3-(the sub-benzene methanamine of 2-hydroxyl-3-oxyethyl group) methyl phenyl ketone is: C
17h
18nO
4, molecular weight is: 300.33, and triclinic(crystalline)system, P-1 spacer.
The synthetic method concrete steps of 2-hydroxyl-3-(the sub-benzene methanamine of 2-hydroxyl-3-oxyethyl group) methyl phenyl ketone are:
(1) 1.6 grams of analytical pure 3-oxyethyl group salicylic aldehydes and 40 milliliters of anhydrous methanols are joined in there-necked flask, be heated to dissolve.
(2) under agitation in the solution of step (1) gained, add 40 milliliters of absolute methanol solutions that are dissolved with 1.5 grams of analytical pure 3-amino-2-hydroxy acetophenones.
(3) in the prepared solution of step (2), drip 1.0 milliliters of anhydrous acetic acids, and 60 ℃ of return stirrings 1.5 hours; Be cooled to room temperature, filter, with ethanol solution washing, obtaining red crystals shape product is 2-hydroxyl-3-(the sub-benzene methanamine of 2-hydroxyl-3-oxyethyl group) methyl phenyl ketone, obtains detailed structural information by single crystal diffractometer.
Claims (1)
1. 2-hydroxyl-3-(the sub-benzene methanamine of 2-hydroxyl-3-oxyethyl group) methyl phenyl ketone, is characterized in that the molecular formula of 2-hydroxyl-3-(the sub-benzene methanamine of 2-hydroxyl-3-oxyethyl group) methyl phenyl ketone is: for: C
17h
18nO
4, molecular weight is: 300.33, and triclinic(crystalline)system, P-1 spacer;
The synthetic method step of described 2-hydroxyl-3-(the sub-benzene methanamine of 2-hydroxyl-3-oxyethyl group) methyl phenyl ketone is:
(1) 1.6-1.8 gram of analytical pure 3-oxyethyl group salicylic aldehyde and 40-42 milliliter anhydrous methanol are joined in there-necked flask, be heated to dissolve;
(2) under agitation in the solution of step (1) gained, add 40-42 milliliter to be dissolved with the absolute methanol solution of 1.5-1.7 gram of analytical pure 3-amino-2-hydroxy acetophenone;
(3) drip 1.0-1.4 milliliter anhydrous acetic acid to the prepared solution of step (2), and at 60-70 ℃ of return stirring 1.5-2.0 hour; Be cooled to room temperature, filter, with ethanol solution washing, obtain red crystals shape product 2-hydroxyl-3-(the sub-benzene methanamine of 2-hydroxyl-3-oxyethyl group) methyl phenyl ketone monocrystalline, obtain detailed structural information by single crystal diffractometer.
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106397462A (en) * | 2016-09-13 | 2017-02-15 | 桂林理工大学 | 3-ethoxysalicylidene-3-amino-2-hydroxyacetophenone Schiff base tetranuclear copper complex and synthetic method thereof |
| CN106431973A (en) * | 2016-09-13 | 2017-02-22 | 桂林理工大学 | Acetophenone derivative Schiff base ligand H2etah and synthetic method |
| CN106431971A (en) * | 2016-09-13 | 2017-02-22 | 桂林理工大学 | Acetophenone derivative Schiff base four-kernel complex Ni4(crah)4 and synthesis method |
| CN106431966A (en) * | 2016-09-13 | 2017-02-22 | 桂林理工大学 | 3,5-dichloro salicylaldehyde-3-amino-2-hydroxyacetophenone Schiff base tetranuclear copper complex and synthesis method |
| CN106431975A (en) * | 2016-09-13 | 2017-02-22 | 桂林理工大学 | Acetylbenzene derivative schiff-base ligand H2dbah and synthetic method |
| CN106431976A (en) * | 2016-09-13 | 2017-02-22 | 桂林理工大学 | Nickel compound of 2-hydroxyacetophenone derivative Schiff base and synthetic method |
| CN106431967A (en) * | 2016-09-13 | 2017-02-22 | 桂林理工大学 | Method for synchronizing 2-hydroxyl acetophenone derivative Schiff base nickel Ni4(ebyl)4 |
| CN106431974A (en) * | 2016-09-13 | 2017-02-22 | 桂林理工大学 | 3,5-dichlorosalicylaldehyde 3-amino-2-hydroxyacetophenone Schiff base ligand and synthesis method |
| CN106431972A (en) * | 2016-09-13 | 2017-02-22 | 桂林理工大学 | Acetophenone derivative Schiff base ligand H2brah and synthesis method |
| CN106496250A (en) * | 2016-09-13 | 2017-03-15 | 桂林理工大学 | 5 bromosalicylaldehydes contracting 3 amino, 2 hydroxy acetophenone schiff bases dicopper complex4-amino-3 and synthetic method |
| CN106496251A (en) * | 2016-09-13 | 2017-03-15 | 桂林理工大学 | 3 ethoxy salicylaldehydes contracting 3 amino, 2 hydroxy acetophenone schiff bases mononuclear copper complex and synthetic method |
| CN106854216A (en) * | 2016-09-13 | 2017-06-16 | 桂林理工大学 | 3,5 Dibromosalicylaldehydes contracting the hydroxy acetophenone schiff bases copper complex of 3 amino 2 and synthetic method |
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2014
- 2014-02-19 CN CN201410056166.5A patent/CN103804223A/en active Pending
Non-Patent Citations (1)
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| 江光奇: "邻香草醛缩邻氨基酚Schiff碱的合成及晶体结构", 《化学研究》 * |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106397462A (en) * | 2016-09-13 | 2017-02-15 | 桂林理工大学 | 3-ethoxysalicylidene-3-amino-2-hydroxyacetophenone Schiff base tetranuclear copper complex and synthetic method thereof |
| CN106431973A (en) * | 2016-09-13 | 2017-02-22 | 桂林理工大学 | Acetophenone derivative Schiff base ligand H2etah and synthetic method |
| CN106431971A (en) * | 2016-09-13 | 2017-02-22 | 桂林理工大学 | Acetophenone derivative Schiff base four-kernel complex Ni4(crah)4 and synthesis method |
| CN106431966A (en) * | 2016-09-13 | 2017-02-22 | 桂林理工大学 | 3,5-dichloro salicylaldehyde-3-amino-2-hydroxyacetophenone Schiff base tetranuclear copper complex and synthesis method |
| CN106431975A (en) * | 2016-09-13 | 2017-02-22 | 桂林理工大学 | Acetylbenzene derivative schiff-base ligand H2dbah and synthetic method |
| CN106431976A (en) * | 2016-09-13 | 2017-02-22 | 桂林理工大学 | Nickel compound of 2-hydroxyacetophenone derivative Schiff base and synthetic method |
| CN106431967A (en) * | 2016-09-13 | 2017-02-22 | 桂林理工大学 | Method for synchronizing 2-hydroxyl acetophenone derivative Schiff base nickel Ni4(ebyl)4 |
| CN106431974A (en) * | 2016-09-13 | 2017-02-22 | 桂林理工大学 | 3,5-dichlorosalicylaldehyde 3-amino-2-hydroxyacetophenone Schiff base ligand and synthesis method |
| CN106431972A (en) * | 2016-09-13 | 2017-02-22 | 桂林理工大学 | Acetophenone derivative Schiff base ligand H2brah and synthesis method |
| CN106496250A (en) * | 2016-09-13 | 2017-03-15 | 桂林理工大学 | 5 bromosalicylaldehydes contracting 3 amino, 2 hydroxy acetophenone schiff bases dicopper complex4-amino-3 and synthetic method |
| CN106496251A (en) * | 2016-09-13 | 2017-03-15 | 桂林理工大学 | 3 ethoxy salicylaldehydes contracting 3 amino, 2 hydroxy acetophenone schiff bases mononuclear copper complex and synthetic method |
| CN106854216A (en) * | 2016-09-13 | 2017-06-16 | 桂林理工大学 | 3,5 Dibromosalicylaldehydes contracting the hydroxy acetophenone schiff bases copper complex of 3 amino 2 and synthetic method |
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Application publication date: 20140521 |