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Method for synthesizing Nitro-PAPS

A technology of phenol and propylamino, which is applied in the synthesis field of Nitro-PAPS, which can solve the problems of limited application range, high price, and long delivery cycle.

Inactive Publication Date: 2018-09-21
HUNAN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, Nitro-PAPS is currently expensive, and there are few literature / patent reports on its synthesis method. There are still few domestic manufacturers that can supply high-purity Nitro-PAPS in large quantities, and the long delivery cycle directly limits its application range.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] The synthesis of embodiment 1.3-(propylamino)phenol

[0019] Weigh 10.0 g (91.6 mmol) of m-aminophenol and dissolve it in 150 mL of absolute ethanol, then add 22.4 g (137.4 mmol) of bromopropane, and stir at room temperature for 20 hours. 10 g of the product 3-(propylamino)phenol was isolated with a yield of 72.2%. 1 H NMR (500 MHz, CDCl 3 ) δ 7.01 (t, J = 8.0 Hz,1H), 6.20 (m, 2H), 6.09 (t, J = 2.2 Hz, 1H), 3.02 (t, J = 7.2 Hz, 2H), 1.61(h, J = 7.3 Hz, 2H), 0.98 (t, J = 7.4, 3H).

Embodiment 2

[0020] Example 2. Synthesis of 3-(N-n-propyl-N-sulfonic acid propylamino)phenol

[0021] Take 3.0 g (19.8 mmol) of 3-(propylamino)phenol and add it to 20 mL of absolute ethanol, then add 2.42 g (19.8 mmol) of 1,3-propane sultone, reflux for 3 hours, and then distill a part Ethanol, after the reaction system was cooled to room temperature, filtered, the filter cake was washed 3 times with cold deionized water, and vacuum-dried to obtain 4.1 g of 3-(N-n-propyl-N-sulfonic acid propylamino)phenol with a yield of 75.6 %. 1 H NMR (500 MHz, DMSO -d 6 ) δ 11.53 (s, 1H), 10.21 (s, 1H), 7.36 (s,1H), 7.06 (s, 2H), 6.90 (s, 1H), 3.69 (s, 1H), 3.61 (s, 1H) , 3.45 (d, J = 8.2Hz, 2H), 2.61 (t, J = 6.7 Hz, 2H), 1.81 (s, 1H), 1.72 (s, 1H), 1.41 (s, 1H), 1.24 (s, 1H), 0.83 (t, J = 7.4, 3H).

Embodiment 3

[0022] Example 3. Synthesis of 2-(5-nitro-2-pyridylazo)-5-(N-propyl-N-sulfopropylamino)phenol disodium salt (Nitro-PAPS)

[0023] Weigh 10.0 g (36.6 mmol) of 3-(N-n-propyl-N-sulfonic acid propylamino) phenol into a round bottom flask, then slowly add 10.92 g (58.5 mmol) of 5-nitro-2 -Aminopyridine diazonium salt solution, continuously feed carbon dioxide gas into the reaction system under stirring at room temperature, stir and react at room temperature for 14 hours, filter after the reaction is completed, wash the filter cake twice with ice ethanol, and alkalinize the obtained solid to obtain Nitro- PAPS 10.5 g, yield 67.8%. 1 H NMR (500 MHz, DMSO -d 6 ) δ 8.96(d, J = 2.8 Hz, 1H), 8.32 (dd, J = 9.6, 2.7 Hz, 1H), 7.05 (m, 2H), 6.85 (m,2H), 3.66 (m, 2H), 3.46 (d, J = 8.7 Hz, 2H), 2.62 (t, J = 6.7 Hz, 2H), 1.77(m, 2H), 1.33 (m, 2H), 0.83 (t, J = 7.4, 3H).

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PUM

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Abstract

The invention discloses a method for synthesizing Nitro-PAPS. The chemical structural formula of the Nitro-PAPS is shown in the description. The Nitro-PAPS serves as commercialized hypersensitive colorimetric reagent for detecting Fe(II) in serum, and is also used for detecting zinc in the serum, has the advantages of high sensitivity, good accuracy, simple and stable reagent, small interference,rapid, simple and convenient operation and the like, and is widely used in biochemical detection. The price of the Nitro-PAPS is expensive, and the literature and patent reports for the synthesis method of the Nitro-PAPS are few, therefore, the invention provides a simple efficient synthesis method with high yield, mild reaction condition and very suitable for industrialized production. Accordingto the method, cheap m-aminophenol serves as a raw material, the m-aminophenol, bromopropane and 1,3-propane sultone are subjected to two-step nucleophilic substitution reaction, lastly, the m-aminophenol and diazonium salt of 2-amino-5-nitropyridine are coupled, and the Nitro-PAPS is synthesized by three steps with a high yield. The whole synthesis technology is simple and efficient, has low cost, and is an economically feasible industrialized production method.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and in particular relates to a synthesis method of Nitro-PAPS. Background technique [0002] As a commercial highly sensitive colorimetric reagent for detecting Fe(II) in serum, Nitro-PAPS can also be used to determine micromolar content of Cu and Zn. It has the advantages of less serum consumption, no protein removal, and a single stable reagent It is widely used in clinical detection / diagnosis due to its fast, simple operation, sensitive and reliable results (Clinica Chimica Acta, 1988, 171, 19-27; Analytica Chimica Acta, 2006, 557, 387-392; Analytica Chimica Acta, 1997, 345 , 139-146). However, Nitro-PAPS is currently expensive, and there are few literature / patent reports on its synthesis method. There are still few domestic manufacturers that can supply high-purity Nitro-PAPS in large quantities, and the long supply cycle directly limits its application range. Therefore, it is of ...

Claims

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Application Information

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IPC IPC(8): C07D213/76
CPCC07D213/76
Inventor 尹鹏徐晨露甘亚兵喻婷尹国兴张友玉
Owner HUNAN NORMAL UNIVERSITY
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