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Method for preparing 6-chlorine-4-trifluoromethyl-3-cyanopyridine

A technology of trifluoromethyl and cyanopyridine, applied in the field of chemistry, can solve the problems of long process steps, harsh operating conditions, complicated operations, etc., and achieves the effects of low reaction cost, short reaction steps, and easy operation.

Active Publication Date: 2014-04-02
贵州威顿晶磷电子材料股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The above-mentioned process for preparing 6-chloro-4-trifluoromethyl-3-cyanopyridine is relatively long, and the operation is relatively complicated. In this route, the carbonyl insertion reaction process needs to be reacted at a low temperature of -78°C, and the operating conditions are relatively harsh.

Method used

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  • Method for preparing 6-chlorine-4-trifluoromethyl-3-cyanopyridine

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Embodiment 1

[0037] A preparation method of 6-chloro-4-trifluoromethyl-3-cyanopyridine, comprising the steps of:

[0038] (1) 2-chloro-6-methoxy-4-trifluoromethyl-3-cyanopyridine ( )Synthesis

[0039] Dissolve 90 g of 2,6-dichloro-4-trifluoromethyl-3-cyanopyridine in 450 g of methanol, add 279 g of sodium methoxide, and react at room temperature for 220 minutes. The reaction is complete as detected by thin-layer chromatography. Spin to dry methanol, add 400g of distilled water was extracted twice with 200g ethyl acetate, and the organic phase was taken and washed with anhydrous Na 2 SO 4 Dry for 2 hours, filter, and spin-dry to obtain 2-chloro-6-methoxy-4-trifluoromethyl-3-cyanopyridine (78.3 g) as an oil, with a yield of 88.6%.

[0040] (2) Synthesis of 6-methoxy-4-trifluoromethyl-3-cyanopyridine (Ⅲ)

[0041] Dissolve 80 g of the obtained 2-chloro-6-methoxy-4-trifluoromethyl-3-cyanopyridine in 400 g of methanol, add 8 g of palladium carbon, control the pressure at 1.5 MPa, replace hy...

Embodiment 2

[0049] A preparation method of 6-chloro-4-trifluoromethyl-3-cyanopyridine, comprising the steps of:

[0050] (1) 2-chloro-6-methoxy-4-trifluoromethyl-3-cyanopyridine ( )Synthesis

[0051] Dissolve 90 g of 2,6-dichloro-4-trifluoromethyl-3-cyanopyridine in 500 g of methanol, add 360 g of sodium methoxide, and react at room temperature for 200 minutes. It is detected by thin-layer chromatography that the reaction is complete, spin dry methanol, and add 450g of distilled water, extracted twice with 250g of ethyl acetate, take the organic phase, and use anhydrous Na 2 SO 4 Dried for 2 hours, filtered, and spin-dried to obtain oily 2-chloro-6-methoxy-4-trifluoromethyl-3-cyanopyridine (78.9 g), with a yield of 89.3%.

[0052] (2) Synthesis of 6-methoxy-4-trifluoromethyl-3-cyanopyridine (Ⅲ)

[0053] Dissolve 80 g of the obtained 2-chloro-6-methoxy-4-trifluoromethyl-3-cyanopyridine in 620 g of methanol, add 8 g of platinum oxide, control the pressure at 1.8 MPa, replace hydrogen f...

Embodiment 3

[0061] A preparation method of 6-chloro-4-trifluoromethyl-3-cyanopyridine, comprising the steps of:

[0062] (1) 2-chloro-6-methoxy-4-trifluoromethyl-3-cyanopyridine ( )Synthesis

[0063] Dissolve 90 g of 2,6-dichloro-4-trifluoromethyl-3-cyanopyridine in 600 g of methanol, add 405 g of sodium methoxide, and react at room temperature for 240 minutes. It is detected by thin-layer chromatography that the reaction is complete, spin dry methanol, and add 500g of distilled water, extracted twice with 250g of ethyl acetate, take the organic phase, and use anhydrous Na 2 SO 4 Dry for 2 hours, filter and spin-dry to obtain 2-chloro-6-methoxy-4-trifluoromethyl-3-cyanopyridine (80.57 g) as an oil, with a yield of 91.2%.

[0064] (2) Synthesis of 6-methoxy-4-trifluoromethyl-3-cyanopyridine (Ⅲ)

[0065] Dissolve 80 g of the obtained 2-chloro-6-methoxy-4-trifluoromethyl-3-cyanopyridine in 620 g of methanol, add 8 g of palladium carbon, control the pressure at 1.8 MPa, replace hydrogen ...

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Abstract

The invention discloses a method for preparing 6-chlorine-4-trifluoromethyl-3-cyanopyridine. The method comprises steps of synthesizing 2-chlorine-6-methoxy-4-trifluoromethyl-3-cyanopyridine, synthesizing 6-methoxy-4-trifluoromethyl-3-cyanopyridine, synthesizing 6-hydroxy-4-trifluoromethyl-3-cyanopyridine, and synthesizing 6-chlorine-4-trifluoromethyl-3-cyanopyridine. The method has high productivity and short reaction steps, is simple to operate, is efficient and is easy to carry out.

Description

technical field [0001] The invention belongs to the technical field of chemistry, and in particular relates to a preparation method of 6-chloro-4-trifluoromethyl-3-cyanopyridine. [0002] Background technique [0003] 6-Chloro-4-trifluoromethyl-3-cyanopyridine is an important intermediate in drug synthesis and can be applied to drug synthesis for the treatment of prostate cancer (see Guo Chuangxing et al. Bioorganic and Medicinal Chemistry Letters, 2012, 22( 2): 1230-1236,); the synthesis of high-efficiency chiral lactams (see Ornilas et al. Tetrahedron Letters, 2011, 52 (37): 4760-4763,); and the synthesis of drugs for the treatment of immunity and tumors ( See patent PCT Int Appl., 2009152133, 2009). The relevant patent documents of the synthetic route of 6-chloro-4-trifluoromethyl-3-cyanopyridine are reported as follows: [0004] PCT Int Appl., 2009152133, 2009, Wishart (Wishart) etc. reported the synthetic route of 6-chloro-4-trifluoromethyl-3-cyanopyridine, the speci...

Claims

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Application Information

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IPC IPC(8): C07D213/85
CPCC07D213/85
Inventor 赵春深蒋飚张光祥安丽君刘天柱王思东段炼滕明刚
Owner 贵州威顿晶磷电子材料股份有限公司
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