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Synthesis method of pyrazolone derivatives by solid acid catalysis

A synthesis method and solid acid technology, which is applied in the field of synthesis of pyrazolone derivatives, can solve the problems of corrosive post-treatment, excessive reagent/catalyst, high temperature and other problems in the reaction process, and achieve recyclable catalyst, non-toxic and cheap catalyst , the effect of mild reaction conditions

Inactive Publication Date: 2014-07-02
TIANJIN POLYTECHNIC UNIV
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0003] There are many reports on the synthetic methods of 4,4'-arymethylene-bis(1-phenyl-3-methyl-5-pyrazolone), and these reports often have high temperature, excessive reagent / catalyst, reaction time long time, low yield of target product, corrosiveness of the reaction process and cumbersome post-treatment, etc.

Method used

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  • Synthesis method of pyrazolone derivatives by solid acid catalysis
  • Synthesis method of pyrazolone derivatives by solid acid catalysis
  • Synthesis method of pyrazolone derivatives by solid acid catalysis

Examples

Experimental program
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Effect test

Embodiment 1

[0018] Example 1 Add 1mmol of benzaldehyde, 2mmol of 1-phenyl-3-methyl-5-pyrazolone, and 0.05mmol of PVP-HSO to a 100ml three-necked flask 4 With 8ml ethanol, react for a certain period of time under reflux conditions, and the reaction is detected by TLC. After the completion of the reaction, add 20ml of water, stir, filter, dry, cross a silica gel column (V 石油醚 :V 乙酸乙酯 =1:2~1:8), to get product 4-[(5-hydroxyl-3-methyl-1-phenyl-1H-4-pyrazolyl)-phenyl-methyl]-5-methyl -2-Phenyl-1,2-dihydro-pyrazolin-3-one, white solid, yield 71%.

[0019] m.p.=169-171℃; IR (KBr): 3354, 3060, 2930, 2596, 1602, 1575, 1500, 1436, 1371, 1028, 826, 782, 735, 687cm -1 ; 1 H NMR (300MHz, DMSO-d 6 )δ: 1.98(s, 1H, NH), 2.32(s, 6H, 2×CH 3 ), 4.96(s, 1H, CH), 7.23~7.33(m, 7H, ArH), 7.42~7.47(m, 4H, ArH), 7.69~7.72(d, 4H, ArH), 13.79(brs, 1H, OH); MS: M + 436;Anal.calcd for C 27 h 24 N 4 o 2 : C, 74.29; H, 5.54; N, 12.84; Found: C, 74.20; H, 5.45; N, 12.76.

Embodiment 2

[0020] Example 2 Add 1mmol of 2-methoxybenzaldehyde, 2mmol of 1-phenyl-3-methyl-5-pyrazolone, and 0.1mmol of PVP-HSO to a 100ml three-necked flask 4 With 8ml ethanol, react for a certain period of time under reflux conditions, and the reaction is detected by TLC. After the completion of the reaction, add 20ml of water, stir, filter, dry, cross a silica gel column (V 石油醚 :V 乙酸乙酯 =1:2~1:8), to get product 4-[(5-hydroxyl-3-methyl-1-phenyl-1H-4-pyrazolyl)-phenyl-methyl]-5-methyl -2-(2-methoxyphenyl)-1,2-dihydro-pyrazolin-3-one, yellow solid, yield 87%.

[0021] m.p.=210-213℃; IR (KBr): 3448, 3052, 2926, 1592, 1581, 1508, 1410, 1251, 1036, 849, 752, 681cm -1 ; 1 H NMR (300MHz, DMSO-d 6 )δ: 1.98(s, 1H, NH), 2.27(s, 6H, 2×CH 3 ), 3.82 (s, 3H, OCH 3 ), 5.19(s, 1H, CH), 6.87~6.96(m, 2H, ArH), 7.17~7.27(m, 3H, ArH), 7.41~7.46(m, 4H, ArH), 7.58~7.61(d, 1H, ArH), 7.68~7.71 (d, 4H, ArH), 13.95 (brs, 1H, OH); MS: M + 466; Anal.calcd for C 28 h 26 N 4 o 3 : C, 72.09; H, 5.62; N,...

Embodiment 3

[0022] Example 3 Add 1mmol of 4-hydroxybenzaldehyde, 2mmol of 1-phenyl-3-methyl-5-pyrazolone, and 0.2mmol of PVP-HSO to a 100ml three-necked flask 4 With 8ml ethanol, react for a certain period of time under reflux conditions, and the reaction is detected by TLC. After the completion of the reaction, add 20ml of water, stir, filter, dry, cross a silica gel column (V 石油醚 :V 乙酸乙酯 =1:2~1:8), to get product 4-[(5-hydroxyl-3-methyl-1-phenyl-1H-4-pyrazolyl)-phenyl-methyl]-5-methyl -2-(4-Hydroxyphenyl)-1,2-dihydro-pyrazolin-3-one, yellow solid, yield 89%.

[0023] m.p.=157-159℃; IR(KBr): 3425, 3061, 2926, 1602, 1499, 1408, 1292, 810, 752, 674cm -1 ; 1 H NMR (300MHz, DMSO-d 6 )δ: 1.91(s, 1H, NH), 2.29(s, 6H, 2×CH 3 ), 4.85(s, 1H, CH), 6.64~6.67(d, 2H, ArH), 7.02~7.05(d, 2H, ArH), 7.24~7.28(m, 2H, ArH), 7.41~7.47(m, 4H, ArH), 7.69~7.71 (m, 4H, ArH), 9.36 (s, 1H, OH), 13.87 (brs, 1H, OH); MS: M + 452;Anal.calcd for C 27 h 24 N 4 o 3: C, 71.67; H, 5.35; N, 12.38; Found: C, 71...

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Abstract

The invention discloses a synthesis method of pyrazolone derivatives by solid acid catalysis. A series of the pyrazolone derivatives are produced by subjecting various substituted aromatic aldehydes or fatty aldehydes and 1-phenyl-3-methyl-5-pyrazolone and aromatic aldehydes to condensation under the catalysis of a solid acid PVP-HSO4. The method has advantages of short reaction time, high yield, simple operation, and capability of being environmental friendly, and the like. The catalyst can be recycled and reutilized.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and is specifically designed to synthesize pyrazolone derivatives. Background technique [0002] Pyrazolone derivatives are important intermediates in organic synthesis. They have a wide range of biological activities and have attracted more and more attention from chemists. They can be used as anti-inflammatory agents, antipyretics, antibacterial agents, and antidepressants. Among them, 4,4'-aryl methylene-bis(1-phenyl-3-methyl-5-pyrazolone) is also used in the extraction of bactericides, pesticides, insecticides, dyes, etc., even as metal ions Drugs are also used. [0003] There are many reports on the synthetic methods of 4,4'-arymethylene-bis(1-phenyl-3-methyl-5-pyrazolone), and these reports often have high temperature, excessive reagent / catalyst, reaction time long time, low yield of the target product, corrosiveness of the reaction process, and cumbersome post-treatment. Contents of th...

Claims

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Application Information

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IPC IPC(8): B01J31/06C07D231/26
CPCY02P20/584
Inventor 臧洪俊李大庆吴长春於年琴程博闻
Owner TIANJIN POLYTECHNIC UNIV
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