8-hydroxyquinoline and preparation method thereof

Abstract

The invention discloses 8-hydroxyquinoline and a preparation method thereof. The preparation method comprises the following steps: (1) preparing a reaction reagent A, namely, mixing ortho-aminophenol and o-nitrophenol; (2) preparing a reaction reagent B, namely, mixing formic acid and acrolein, and adding a zeolite molecular sieve into a mixed liquid of the formic acid and the acrolein; (3) heating the reaction reagent A to 95-100 DEG C, adding the reaction reagent B, enabling the component to react under a condition of constant-temperature stirring, filtering, and cooling the filtrate to the room temperature; and (4) neutralizing the filtrate obtained in the step (3) by using a 40% sodium hydroxide solution, filtering again, and performing reduced pressure distillation, thereby obtaining a final expected product, that is, 8-hydroxyquinoline. Compared with the prior art, the preparation method has the advantages of rapid reaction, gentle condition and high yield and is particularly applicable to industrial production.

Description

Technical field:

[0001] The invention relates to the technical field of biomedicine, in particular to 8-hydroxyquinoline and a preparation method thereof. Background technique:

[0002] 8-Hydroxyquinoline is an important intermediate in pharmaceutical synthesis, and its synthesis process and preparation of derivatives are one of the hotspots in the fields of medicine and chemical engineering. 8-Hydroxyquinoline can be directly used as a disinfectant, and its derivatives also play an important role in the medical field. For example, its halogenated derivatives, nitrates, etc. are important raw materials for synthetic drugs, and can be used as synthetic pesticides, dyes and other An important intermediate for functional materials. In addition, 8-hydroxyquinoline is also an excellent metal ion chelating agent, which is widely used in metallurgical industry and analytical chemistry for chemical analysis of metal elements, photometric analysis, metal ion extraction and metal ant...

Examples

Embodiment 1

[0020] (1) Configure reaction reagent A: mix 1mol o-aminophenol and 1.2mol o-nitrophenol to prepare o-aminophenol / o-nitrophenol mixed solution;

[0021] (2) Prepare reaction reagent B: mix 5 mol of formic acid and 3 mol of acrolein, add zeolite molecular sieve to formic acid / acrolein mixture, the mass ratio of zeolite molecular sieve to formic acid / acrylic acid mixture is 0.5:1;

[0022] (3) Heating Reagent A to 95-100°C, then adding Reagent B, reacting for 1 hour under constant temperature and stirring, filtering, and cooling the filtrate to room temperature;

[0023] (4) Neutralize the filtrate described in step (3) with 40% sodium hydroxide solution, filter again, and distill under reduced pressure to obtain the final desired product 8-hydroxyquinoline.

[0024] Experimental results show that the yield is 87.2%.

Embodiment 2

[0026] (1) Configure reaction reagent A: mix 1mol o-aminophenol and 1.5mol o-nitrophenol to prepare o-aminophenol / o-nitrophenol mixed solution;

[0027] (2) Prepare reaction reagent B: mix 6 mol of formic acid and 3 mol of acrolein, add zeolite molecular sieve to the formic acid / acrolein mixture, the mass ratio of zeolite molecular sieve to formic acid / acrylic acid mixture is 0.5:1;

[0028] (3) Heating Reagent A to 95-100°C, then adding Reagent B, reacting for 2 hours under constant temperature and stirring, filtering, and cooling the filtrate to room temperature;

[0029] (4) Neutralize the filtrate described in step (3) with 40% sodium hydroxide solution, filter again, and distill under reduced pressure to obtain the final desired product 8-hydroxyquinoline.

[0030] Experimental results show that the yield is 95.6%.

Embodiment 3

[0032] (1) Configure reaction reagent A: mix 2mol o-aminophenol and 3mol o-nitrophenol to prepare o-aminophenol / o-nitrophenol mixed solution;

[0033] (2) Prepare reaction reagent B: mix 8 mol of formic acid and 6 mol of acrolein, add zeolite molecular sieve to formic acid / acrolein mixture, the mass ratio of zeolite molecular sieve to formic acid / acrylic acid mixture is 0.5:1;

[0034] (3) Heating Reagent A to 95-100°C, then adding Reagent B, reacting for 1.5h under constant temperature and stirring, filtering, and cooling the filtrate to room temperature;

[0035] (4) Neutralize the filtrate described in step (3) with 40% sodium hydroxide solution, filter again, and distill under reduced pressure to obtain the final desired product 8-hydroxyquinoline.

[0036] Experimental results show that the yield is 82.1%.

Technical field:

[0001] The invention relates to the technical field of biomedicine, in particular to 8-hydroxyquinoline and a preparation method thereof. Background technique:

[0002] 8-Hydroxyquinoline is an important intermediate in pharmaceutical synthesis, and its synthesis process and preparation of derivatives are one of the hotspots in the fields of medicine and chemical engineering. 8-Hydroxyquinoline can be directly used as a disinfectant, and its derivatives also play an important role in the medical field. For example, its halogenated derivatives, nitrates, etc. are important raw materials for synthetic drugs, and can be used as synthetic pesticides, dyes and other An important intermediate for functional materials. In addition, 8-hydroxyquinoline is also an excellent metal ion chelating agent, which is widely used in metallurgical industry and analytical chemistry for chemical analysis of metal elements, photometric analysis, metal ion extraction and metal ant...

Examples

Embodiment 1

[0020] (1) Configure reaction reagent A: mix 1mol o-aminophenol and 1.2mol o-nitrophenol to prepare o-aminophenol / o-nitrophenol mixed solution;

[0021] (2) Prepare reaction reagent B: mix 5 mol of formic acid and 3 mol of acrolein, add zeolite molecular sieve to formic acid / acrolein mixture, the mass ratio of zeolite molecular sieve to formic acid / acrylic acid mixture is 0.5:1;

[0022] (3) Heating Reagent A to 95-100°C, then adding Reagent B, reacting for 1 hour under constant temperature and stirring, filtering, and cooling the filtrate to room temperature;

[0023] (4) Neutralize the filtrate described in step (3) with 40% sodium hydroxide solution, filter again, and distill under reduced pressure to obtain the final desired product 8-hydroxyquinoline.

[0024] Experimental results show that the yield is 87.2%.

Embodiment 2

[0026] (1) Configure reaction reagent A: mix 1mol o-aminophenol and 1.5mol o-nitrophenol to prepare o-aminophenol / o-nitrophenol mixed solution;

[0027] (2) Prepare reaction reagent B: mix 6 mol of formic acid and 3 mol of acrolein, add zeolite molecular sieve to the formic acid / acrolein mixture, the mass ratio of zeolite molecular sieve to formic acid / acrylic acid mixture is 0.5:1;

[0028] (3) Heating Reagent A to 95-100°C, then adding Reagent B, reacting for 2 hours under constant temperature and stirring, filtering, and cooling the filtrate to room temperature;

[0029] (4) Neutralize the filtrate described in step (3) with 40% sodium hydroxide solution, filter again, and distill under reduced pressure to obtain the final desired product 8-hydroxyquinoline.

[0030] Experimental results show that the yield is 95.6%.

Embodiment 3

[0032] (1) Configure reaction reagent A: mix 2mol o-aminophenol and 3mol o-nitrophenol to prepare o-aminophenol / o-nitrophenol mixed solution;

[0033] (2) Prepare reaction reagent B: mix 8 mol of formic acid and 6 mol of acrolein, add zeolite molecular sieve to formic acid / acrolein mixture, the mass ratio of zeolite molecular sieve to formic acid / acrylic acid mixture is 0.5:1;

[0034] (3) Heating Reagent A to 95-100°C, then adding Reagent B, reacting for 1.5h under constant temperature and stirring, filtering, and cooling the filtrate to room temperature;

[0035] (4) Neutralize the filtrate described in step (3) with 40% sodium hydroxide solution, filter again, and distill under reduced pressure to obtain the final desired product 8-hydroxyquinoline.

[0036] Experimental results show that the yield is 82.1%.