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Prepn process of 3-nitro salicylaldehyde

A technology for nitrosalicylaldehyde and salicylaldehyde, which is applied in the field of 3-nitrosalicylaldehyde preparation, can solve the problems of difficult product separation, complicated operation, long reaction time and the like, and achieves convenient product separation, improved selectivity, The effect of easy operation

Inactive Publication Date: 2007-08-22
HUAIYIN TEACHERS COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, 3-nitrosalicylaldehyde is mainly prepared by nitration reaction with mixed acid, namely concentrated sulfuric acid and concentrated nitric acid, as nitrating reagents, but this method has long reaction time, complicated operation, and difficult separation of products

Method used

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  • Prepn process of 3-nitro salicylaldehyde
  • Prepn process of 3-nitro salicylaldehyde
  • Prepn process of 3-nitro salicylaldehyde

Examples

Experimental program
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Effect test

Embodiment 1

[0014] Add 0.61g (5mmol) salicylaldehyde, 10mL acetic acid with a volume fraction of 50%, 0.40g (1mmol) polyethylene glycol-400, 2.74g (5mmol) cerium ammonium nitrate in a 50ml Erlenmeyer flask, heat to 30°C, Reaction 1.2h, wherein, TLC traces, developer is acetone-petroleum ether, stops heating, stirs; The reaction product is poured into ice water, and the yellow solid that precipitates is 3-nitrosalicylaldehyde and 5-nitrosalicylaldehyde Mixture, add 1% sodium hydroxide solution 4.0mL (0.001mmol) in the mixture, make 3-nitrosalicylaldehyde and 5-nitrosalicylaldehyde all change into sodium salt completely, utilize two kinds of sodium salts in water solubility Difference, adjust the pH value to 3.0 with diluted hydrochloric acid, wash with water 5 times, each 30mL, can obtain 3-nitrosalicylaldehyde. Weight: 0.32g, yield: 76.6%, mp: 107-110°C, consistent with literature values, IR: Vmax (KBr tablet, cm -1 ), 3069 (-OH), 1640 (-CHO), 1627, 1472 (skeleton vibration), 1527, 1342 ...

Embodiment 2

[0016] Add 0.61g (5mmol) of salicylaldehyde, 10mL of 50% volume fraction of acetic acid, 0.60g (1.5mmol) of polyethylene glycol-400, 3.56g (6.5mmol) of ammonium cerium nitrate in a 50ml Erlenmeyer flask, and heat to 70°C , reacted for 2.0h, wherein, TLC traced, the developer was acetone-petroleum ether, stopped heating and stirring; the reaction product was poured into ice water to obtain a yellow solid, which was 3-nitrosalicylaldehyde and 5-nitrosalicylaldehyde The mixture of aldehydes, add 1% sodium hydroxide solution 4.0mL (0.001mmol) in the mixture, make 3-nitrosalicylaldehyde and 5-nitrosalicylaldehyde all change into sodium salt completely, utilize two kinds of sodium salts in water According to the difference in solubility, adjust the pH value to 4 with diluted hydrochloric acid, and then wash 5 times with 30 mL each time to obtain 3-nitrosalicylaldehyde. Weight: 0.31 g, yield: 74.3%, mp: 108.5-110°C, consistent with literature values. IR: Vmax (KBr tablet, cm -1 ), ...

Embodiment 3

[0018] In a 1500ml round bottom flask, add 61g (500mmol) salicylaldehyde, 1000mL50% (volume fraction) acetic acid, 50g (125mmol) polyethylene glycol-400, 328.8g (600mmol) cerium ammonium nitrate, heated to 50 ℃, reaction 1.6 h, wherein, TLC traces, developing agent is acetone-petroleum ether, stop heating, stir; Pour reaction product into ice water, separate out yellow solid, be the mixture of 3-nitrosalicylaldehyde and 5-nitrosalicylaldehyde , add 1% sodium hydroxide solution 400mL (0.1mmol) in the mixture, make 3-nitrosalicylaldehyde and 5-nitrosalicylaldehyde all change into sodium salt completely, utilize the difference of solubility of two kinds of sodium salts in water, Adjust the pH value to 5 with diluted hydrochloric acid, and then wash with water 6 times to obtain 3-nitrosalicylaldehyde. Weight: 31.5g, productive rate: 75.4%, mp: 108-110 ℃, consistent with literature value, IR: Vmax (KBr tablet, cm -1 ), 3069 (-OH), 1640 (-CHO), 1626, 1470 (skeleton vibration), 1526...

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Abstract

The process of preparing 3-nitro salicylaldehyde adopts ammonium cerium nitrate and salicylaldehyde as material, acetic acid as solvent, polyglycol-400 as phase transferring catalyst, and ammonium cerium nitrate as nitrifier. The preparation process includes dissolving salicylaldehyde, ammonium cerium nitrate and polyglycol-400 in the molar ratio of 1 to 1.0-1.3 to 0.2-0.3 in acetic acid, heating to 30-70 deg.c to react for 1.2-2.0 hr, pouring the reaction product into icy water to separate yellow mixture of 3-nitro salicylaldehyde and 5-nitro salicylaldehyde, dissolving the mixture in sodium hydroxide solution, regulating pH with dilute hydrochloric acid solution to 3-5, and water washing for 5-6 times to obtain 3-nitro salicylaldehyde. The present invention has simplified operation, shortened reaction time and easy separation.

Description

technical field [0001] The invention relates to a preparation method of a compound, in particular to a preparation method of 3-nitrosalicylaldehyde. Background technique [0002] 3-Nitrosalicylaldehyde is an important intermediate in organic synthesis, which can be used in the preparation of various multidentate ligands, drugs and spiropyran photochromic compounds, etc., and occupies an important position in the field of fine organic chemicals. 3-nitrosalicylaldehyde is the key to generate Schiff's base derivatives. The research results show that some Schiff's base derivatives have biological activities such as anti-cancer, anti-virus, and inhibition of bacterial growth. At present, 3-nitrosalicylaldehyde is mainly prepared by nitration reaction with mixed acid, namely concentrated sulfuric acid and concentrated nitric acid, as nitrating reagents. However, the reaction time of this method is long, the operation is complicated, and the product is not easy to separate. Conte...

Claims

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Application Information

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IPC IPC(8): C07C201/08C07C205/44
Inventor 朱惠琴周建峰朱凤霞
Owner HUAIYIN TEACHERS COLLEGE
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