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Method for synthesizing C-5-bit trifluoromethylated 8-aminoquinoline by utilizing micro-channel reaction device under visible light

A technology of microchannel reaction and trifluoromethylation, which is applied in organic chemistry and other fields, can solve problems such as low yield and atom utilization, high requirements for reactor design, poor selectivity, etc., and achieve shortened reaction time and improved Yield, the effect of reducing side reactions

Inactive Publication Date: 2021-01-26
NANJING ADVANCED BIOLOGICAL MATERIALS & PROCESS EQUIP INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The technical problem to be solved by the present invention is to provide a method for introducing a trifluoromethyl group at the C-5 position of an 8-aminoquinoline compound with mild reaction conditions, an efficient and environmentally friendly method for solving the deficiencies of the prior art. There are problems such as high requirements for reactor design, high energy consumption, poor selectivity, low yield and atom utilization.

Method used

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  • Method for synthesizing C-5-bit trifluoromethylated 8-aminoquinoline by utilizing micro-channel reaction device under visible light
  • Method for synthesizing C-5-bit trifluoromethylated 8-aminoquinoline by utilizing micro-channel reaction device under visible light
  • Method for synthesizing C-5-bit trifluoromethylated 8-aminoquinoline by utilizing micro-channel reaction device under visible light

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] N-(quinolin-8-yl)benzamide (5 mmol, 1.0 equiv) was weighed and dissolved in dimethylformamide (10 mL) and loaded into syringe a. NaCF 3 SO 2(10 mmol, 2.0 equiv) and Eosin Y (0.25 mmol, 5% equiv) were dissolved in water (10 mL) and loaded in syringe b. The reaction solution in a and b enters the reactor with a coil inner diameter of 0.5mm under visible light through the Y-type mixer, the flow rate of the syringe a and b is 0.5mL / min, and the flow rate of the microreactor is 1.0mL / min, the reaction temperature was controlled at 30°C, the residence time was 20min, and the reaction progress was detected by TLC (petroleum ether:ethyl acetate=4:1). 100mL saturated NaHCO 3 (aq) washing, liquid separation, the aqueous phase was extracted with ethyl acetate (150mL×3), the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and the crude product was concentrated with ethyl acetate / n-hexane as solvents respectively Recrystallized wi...

Embodiment 2

[0045] N-(quinolin-8-yl)benzamide (5 mmol, 1.0 equiv) was weighed and dissolved in dimethyl sulfoxide (10 mL) and loaded into syringe a. NaCF 3 SO 2 (10 mmol, 2.0 equiv) and Eosin Y (0.25 mmol, 5% equiv) were dissolved in water (10 mL) and loaded in syringe b. The reaction solution in a and b enters the reactor with a coil inner diameter of 0.5mm under visible light through the Y-type mixer, the flow rate of the syringe a and b is 0.5mL / min, and the flow rate of the microreactor is 1.0mL / min, the reaction temperature was controlled at 30°C, the residence time was 20min, and the reaction progress was detected by TLC (petroleum ether:ethyl acetate=4:1). 100mL saturated NaHCO 3 (aq) washing, liquid separation, the aqueous phase was extracted with ethyl acetate (150mL×3), the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and the crude product was concentrated with ethyl acetate / n-hexane as solvents respectively Recrystallized ...

Embodiment 3

[0047] N-(quinolin-8-yl)benzamide (5 mmol, 1.0 equiv) was weighed and dissolved in dichloromethane (10 mL) and loaded into syringe a. NaCF 3 SO 2 (10 mmol, 2.0 equiv) and Eosin Y (0.25 mmol, 5% equiv) were dissolved in water (10 mL) and loaded in syringe b. The reaction solution in a and b enters the reactor with a coil inner diameter of 0.5mm under visible light through the Y-type mixer, the flow rate of the syringe a and b is 0.5mL / min, and the flow rate of the microreactor is 1.0mL / min, the reaction temperature was controlled at 30°C, the residence time was 20min, and the reaction progress was detected by TLC (petroleum ether:ethyl acetate=4:1). 100mL saturated NaHCO 3 (aq) washing, liquid separation, the aqueous phase was extracted with ethyl acetate (150mL×3), the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and the crude product was concentrated with ethyl acetate / n-hexane as solvents respectively Recrystallized wit...

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Abstract

The invention discloses a method for synthesizing C-5-bit trifluoromethylated 8-aminoquinoline by using a micro-channel reaction device under visible light. The method comprises the following steps: dissolving a 8-aminoquinoline compound in a solvent to obtain a homogeneous solution A, and dissolving eosin Y and NaCF3SO2 in water to obtain a homogeneous solution B; and simultaneously pumping the prepared homogeneous solution A and homogeneous solution B into a micro-mixer of a micro-channel reaction device respectively, mixing, introducing into a micro-channel reactor of the micro-channel reaction device under irradiation of visible light, making reaction, and washing separating, extracting, concentrating, and recrystallizinga reaction effluent, to obtain the product. According to the method, the product of C-5-bit trifluoromethylated 8-aminoquinoline is prepared by using a micro-channel reaction device under visible light irradiation, compared with common reaction, the reaction time is shortened, the reaction conversion rate is increased, and the product yield reaches 79%-93%; the product is stable and additive-free and is beneficial to large-scale production; meanwhile, operationis easy, the safety is high, and the defects of a traditional reaction kettle can be effectively overcome.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a method for synthesizing C-5-position trifluoromethylated 8-aminoquinoline by using a microchannel reaction device under visible light. Background technique [0002] It is known that 8-aminoquinoline is the mother nucleus of many important drugs and active ingredients of insecticides. The core is the most basic structure-active group of the drug, while the substituent affects the structure-activity relationship and metabolism of the drug. The activity of the drug is jointly structured by the core and the substituent. By modifying the 8-aminoquinoline structure, the water-solubility and fat-solubility of the drug can be improved, thereby improving its activity in vivo. [0003] At the same time, studies have shown that the fluorine atom radius and C-F bond distance in nature are similar to the hydrogen atom radius and C-H bond distance, making organisms less discern...

Claims

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Application Information

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IPC IPC(8): C07D215/40
CPCC07D215/40
Inventor 李玉光郭凯黄达李亚军高迪沈磊
Owner NANJING ADVANCED BIOLOGICAL MATERIALS & PROCESS EQUIP INST CO LTD
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