8-acetonitrile oxy imidazo [1,2-a] pyridine-3-carbonitrile preparation method

A technology of acetonitrile oxyimidazole and 2-a, which is applied in the field of preparation of 8-acetonitrile oxyimidazo[1,2-a]pyridine-3-carbonitrile, which can solve the problem of few preparation methods and unfavorable research and promotion and other problems, to achieve the effect of simple post-processing, easy control, and stable product quality

Inactive Publication Date: 2015-09-16
SHANDONG YOUBANG BIOCHEM TECH
View PDF0 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 8-Acetonitrile oxyimidazo[1,2-a]pyridine-3-carbonitrile, as an imidazo[1,2-a]pyridine-3-carbonitrile derivative, is an important intermediate in organic synthesis, mainly It is used in pharmaceutical intermediates, organic synthesis, and can also be used in the production of pesticides and spices. Its preparation methods are rarely recorded in the literature, which is not conducive to the research and promotion of this product and related products.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 8-acetonitrile oxy imidazo [1,2-a] pyridine-3-carbonitrile preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] 600mmol (71.7g) of N,N-dimethylformamide dimethyl acetal is both a solvent and a reaction raw material, react with 2-amino-3-hydroxypyridine (22.0g) at 40°C for 5 hours, and the reaction is completed To obtain N,N-dimethyl-N'-2-(3-hydroxy-pyridinyl)-formamidine intermediate, remove excess N,N-dimethylformamide dimethyl acetal by rotary evaporation, add 120 mL (114g) N,N-dimethylformamide (DMF), NaHCO 3 (25.2g, 300mmol), add bromoacetonitrile (50.1g, 300mmol) according to the ratio of 2-amino-3-hydroxypyridine and bromoacetonitrile 1:1.5, react at 50°C for 10 hours, after the reaction is completed, cool to room temperature, add 600 mL Extract with water and 200 mL ethyl acetate, separate the organic phase, extract the aqueous phase with ethyl acetate (3×200 mL), combine the organic phases, wash with water (2×150 mL), wash with 200 mL saturated brine, anhydrous Na 2 SO 4 After drying, filtering, and concentrating the filtrate, the crude product of 8-acetonitrileoxyimi...

Embodiment 2

[0020] 600mmol (71.7g) N,N-dimethylformamide dimethyl acetal is both a solvent and a reaction material, and 2-amino-3-hydroxypyridine (66g, 600mmol) in a ratio of 1:1 at 70°C After reacting for 6 hours, the N,N-dimethyl-N'-2-(3-hydroxy-pyridinyl)-formamidine intermediate was obtained after the reaction was completed, and the excess N,N-dimethylformamide was removed by rotary evaporation. Methyl acetal, add 120 mL (125 g) dioxane, K 2 CO 3 (20.8g, 150mmol), add bromoacetonitrile (100.2g, 600mmol) according to the ratio of 2-amino-3-hydroxypyridine to bromoacetonitrile 1:1, react at 80°C for 10 hours, after the reaction is completed, cool to room temperature, add 600 mL of water Extract with 200 mL ethyl acetate, separate the organic phase, extract the aqueous phase with ethyl acetate (3×200 mL), combine the organic phases, wash with water (2×150 mL), wash with 200 mL saturated brine, anhydrous Na 2 SO 4 After drying, filtering, and concentrating the filtrate, the crude produ...

Embodiment 3

[0022] 600mmol (71.7g) N,N-dimethylformamide dimethyl acetal is both a solvent and a reaction material, and 2-amino-3-hydroxypyridine (11.0g, 100mmol) in a ratio of 6:1 at 60°C After 5 hours of reaction, the N,N-dimethyl-N'-2-(3-hydroxy-pyridinyl)-formamidine intermediate was obtained after the reaction, and the excess N,N-dimethylformamide was removed by rotary evaporation Dimethyl acetal, add 120 mL (103g) toluene, triethylamine (30.3g, 300mmol) according to the ratio of 2-amino-3-hydroxypyridine to bromoacetonitrile 1:3, add bromoacetonitrile (50.1g, 300mmol), 100 Reaction at ℃ for 8 hours, after the reaction was completed, cool to room temperature, add 600 mL of water and 200 mL of ethyl acetate for extraction, separate the organic phase, extract the aqueous phase with ethyl acetate (3×200 mL), combine the organic phases, and wash with water (2×150 mL), washed with 200 mL saturated brine, anhydrous Na 2 SO 4 After drying, filtering, and concentrating the filtrate, the cr...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The present invention relates to a 8-acetonitrile oxy imidazo [1,2-a] pyridine-3-carbonitrile preparation method. The preparation method comprises the following steps: N, N-dimethylformamide dimethyl acetal is reacted with 2-amino-3-hydroxy pyridine in a certain proportion at 40-100 DEG C to obtain N, N-dimethyl-N '-2-(3-hydroxy-pyridine) yl-formamidine intermediate, under the effect of an alkali, in a certain solvent, the N, N-dimethyl-N '-2-(3-hydroxy-pyridine) yl-formamidine intermediate is reacted with bromoacetonitrile in certain proportion at 50-160 DEG C for 3-15 hours, after the reaction, a 8-acetonitrile oxy imidazo [1,2-a] pyridine-3-carbonitrile crude product is obtained by cooling to room temperature, extracting with ethyl acetate, washing with water and saturated salt water, drying with anhydrous sodium sulfate, rotation evaporation and concentration, and a pure product is obtained by recrystallization of the crude product. Reaction materials are relatively easy to obtain, and are reasonable in prices, reaction conditions are mild, easy to operate, and easy to control, post-processing is simple, product quality is stable, and purity is high.

Description

(1) Technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of 8-acetonitrile oxyimidazo[1,2-a]pyridine-3-carbonitrile. (2) Background technology [0002] The synthesis method of 6-chloroimidazo[1,2-a]pyridine-3-carbonitrile published on 2014.07.02, which discloses the preparation process of imidazo[1,2-a]pyridine-3-carbonitrile derivatives : Add 2-amino-5-chloropyridine (3.86g, 30mmol) and DMF-DM (A 12mL) into a 50mL single-necked round bottom flask, heat and stir the reaction, the reaction temperature is 100-110°C, and the reaction ends after 4h; rotate DMF-DMA was removed by evaporation and transferred to a 100mL flask without further treatment. Directly added 30mL of DMF, 3.78g of sodium bicarbonate and 5.40g of bromoacetonitrile and heated and stirred to react. The reaction temperature was 130-140°C, and the reaction was terminated after 15h. Transfer the reaction mixture to a large beaker, add 2...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 韩猛樊红莉来新胜曹惊涛
Owner SHANDONG YOUBANG BIOCHEM TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap