Preparation method of 2-quinoline amide compound promoted by acidic ionic liquid

Abstract

The invention relates to the technical field of chemical synthesis, in particular to a preparation method of a 2-quinoline amide compound promoted by acidic ionic liquid. A series of 2-quinoline amide compounds are synthesized by taking quinoline nitrogen oxide and acetonitrile as starting raw materials under the promotion of acidic ionic liquid. The method has the advantages of easily available raw materials, simplicity and convenience in operation, mild reaction conditions, economic reaction steps, high yield and the like. Meanwhile, the acidic ionic liquid can be recycled, so that the method has the possibility of realizing industrialization; the synthesized 2-quinoline amide compound can be further derivatized to obtain different types of compounds, and has the potential of being applied to development and research of natural products, drug molecules and functional materials.

Description

Technical Field

[0001] The invention relates to the technical field of chemical synthesis, and in particular to a method for preparing a 2-quinolineamide compound promoted by an acidic ionic liquid. Background Art

[0002] Quinoline and its derivatives are extremely important nitrogen-containing heterocyclic compounds, which have important application value in the fields of medicine and functional materials. As an important member of them, 2-quinolineamide compounds are widely present in natural products, drug molecules and bioactive molecules. At the same time, this type of compound is also a key intermediate for the synthesis of functional material molecules, and the research on its synthesis method has attracted great attention from chemists.

[0003] Prior art generally prepares this type of compound by two types of methods. The first type of method synthesizes 2-quinoline amide compounds by nucleophilic substitution reaction, i.e., amide and 2-halogenated quinoline or 2-aminoquinoline and acyl halide reaction. No matter which reaction form needs to prepare halides in advance, this type of method not only has poor atom economy, but also has shortcomings in environmental friendliness. Another method is to obtain by direct reaction of quinoline nitrogen oxide with amide or nitrile. This type of method avoids the environmental problems caused by preparing halides in advance, and the atomic utilization rate of the reaction is also greatly improved. However, harsher reaction conditions, such as high temperature, or too many reaction steps still limit its wide application in the field of synthesis. Summary of the invention

[0004] The purpose of the present invention is to overcome the above problems and provide a method for preparing a 2-quinolineamide compound, by using an acidic ionic liquid under mild conditions to quickly and efficiently synthesize the 2-quinolineamide compound, and the acidic ionic liquid can be recycled and reused. To achieve the above purpose, the present invention adopts the following technical scheme:

[0005] A method for preparing a 2-quinoline amide compound, using quinoline nitrogen oxide as a raw material, reacting in acetonitrile at 30°C-80°C for 16-24h under the action of an acidic ionic liquid to obtain a 2-quinoline amide compound. The synthetic route is as follows Figure 1 As shown. Among them:

[0006] R is selected from hydrogen (H), alkyl (alkyl), halides (halides), methoxy (OCH 3 ), nitro (NO 2 );

[0007] The molar ratio of quinoline nitrogen oxide to acidic ionic liquid is 1:0.01 to 1:0.1;

[0008] The molar ratio of quinoline nitrogen oxide to acetonitrile is 1:1 to 1:100;

[0009] The molar concentration of quinoline nitrogen oxide is 0.01 mmol / mL to 2 mmol / mL.

[0010] The quinoline nitrogen oxide derivatives include quinoline nitrogen oxides without substituents, and quinoline nitrogen oxide derivatives having electron-donating substituents and electron-withdrawing substituents at the 4-position, 5-position, 6-position, 7-position, and 8-position; the electron-donating substituents include Me and OMe groups; the electron-withdrawing substituents include halides and NO 2 Group.

[0011] Acidic ionic liquids include Figure 1 There are five categories: 1-ethyl-3-butyl imidazolium hydrogen sulfate ionic liquid (IL1), 1,3-dibutyl imidazolium hydrogen sulfate ionic liquid (IL2), 1-ethyl-3-butyl sulfonic acid imidazolium hydrogen sulfate ionic liquid (IL3), 1-butyl-3-butyl sulfonic acid imidazolium hydrogen sulfate ionic liquid (IL4), and 1,3-dibutyl sulfonic acid imidazolium hydrogen sulfate ionic liquid (IL5).

[0012] The solvent includes N,N-dimethylformamide, dimethyl sulfoxide, tetrahydrofuran, ethylene glycol dimethyl ether, dichloromethane, trifluoroethanol, acetone, toluene, chlorobenzene, 1,4-dioxane, and n-hexane.

[0013] Separation methods include recrystallization, column chromatography, etc. The solvents used in the recrystallization method include ethanol, isopropanol, n-hexane, tetrahydrofuran, acetone, ethyl acetate, and dichloromethane; when using the column chromatography method to separate the product, silica gel or alumina can be used as the stationary phase, and the developing solvent is generally a mixed solvent of polar and non-polar, such as ethyl acetate-petroleum ether, ethyl acetate-n-hexane, dichloromethane-petroleum ether, and methanol-petroleum ether.

[0014] Water and ethyl acetate (or dichloromethane) are added to the system after the reaction is completed, so as to separate and recover the acidic ionic liquid. After the acidic ionic liquid is recycled for 5 times, its activity does not decrease significantly.

[0015] The beneficial effects of the present invention are simple operation, mild conditions, environmental friendliness, the acidic ionic liquid can be recycled and reused, it is possible to realize industrialization, and 2-quinolineamide compounds are obtained with a high yield; the 2-quinolineamide compounds synthesized by the method can be further functionalized to obtain various compounds, which are applied to the development and research of natural products, drug molecules and functional materials. BRIEF DESCRIPTION OF THE DRAWINGS

[0016] Figure 1 It is the synthesis route diagram of the present invention.

[0017] Figure 2 is the 2-quinolineacetamide in Example 11 H NMR spectrum.

[0018] Figure 3 is the 2-quinolineacetamide in Example 1 13 C NMR spectrum.

[0019] Figure 4 is the 4-methyl-2-quinolineacetamide in Example 2 1 H NMR spectrum.

[0020] Figure 5 is the 4-methyl-2-quinolineacetamide in Example 2 13 C NMR spectrum.

[0021] Figure 6 is the 4-chloro-2-quinolineacetamide in Example 3 1 H NMR spectrum.

[0022] Figure 7 is the 4-chloro-2-quinolineacetamide in Example 3 13 C NMR spectrum.

[0023] Figure 8 is the 4-chloro-6-fluoro-2-quinolineacetamide in Example 4 1 H NMR spectrum.

[0024] Fig. 9 is the 4-chloro-6-fluoro-2-quinolineacetamide in Example 4 13 C NMR spectrum.

[0025] Fig.10 is the 5-bromo-2-quinolineacetamide in Example 5 1 H NMR spectrum.

[0026] Fig.11 is the 5-bromo-2-quinolineacetamide in Example 5 13 C NMR spectrum.

[0027] Fig.12 is the 5-methoxy-2-quinolineacetamide in Example 6 1 H NMR spectrum.

[0028] Fig.13 is the 5-methoxy-2-quinolineacetamide in Example 6 13 C NMR spectrum.

[0029] Fig.14 is the 6-methyl-2-quinolineacetamide in Example 7 1 H NMR spectrum.

[0030] Fig.15 is the 6-methyl-2-quinolineacetamide in Example 713 C NMR spectrum.

[0031] Fig.16 is the 6-fluoro-2-quinolineacetamide in Example 8 1 H NMR spectrum.

[0032] Fig.17 is the 6-fluoro-2-quinolineacetamide in Example 8 13 C NMR spectrum.

[0033] Fig.18 is the 6-chloro-2-quinolineacetamide in Example 9 1 H NMR spectrum.

[0034] Fig.19 is the 6-chloro-2-quinolineacetamide in Example 9 13 C NMR spectrum.

[0035] Fig. 20 is the 6-bromo-2-quinolineacetamide in Example 10 1 H NMR spectrum.

[0036] Fig.21 is the 6-bromo-2-quinolineacetamide in Example 10 13 C NMR spectrum.

[0037] Fig. 22 is the 6-methoxy-2-quinolineacetamide in Example 11 1 H NMR spectrum.

[0038] Fig.23 is the 6-methoxy-2-quinolineacetamide in Example 11 13 C NMR spectrum.

[0039] Fig.24 is the 6-nitro-2-quinolineacetamide in Example 12 1 H NMR spectrum.

[0040] Fig.25 is the 6-nitro-2-quinolineacetamide in Example 12 13 C NMR spectrum.

[0041] Fig.26 is the 7-methyl-2-quinolineacetamide in Example 13 1 H NMR spectrum.

[0042] Fig. 27 is the 7-methyl-2-quinolineacetamide in Example 13 13 C NMR spectrum.

[0043] Fig.28is 8-methyl-2-quinolineacetamide in Example 14 1 H NMR spectrum.

[0044] Fig.29 is 8-methyl-2-quinolineacetamide in Example 14 13 C NMR spectrum.

[0045] Fig.30 is 8-fluoro-2-quinolineacetamide in Example 15 1 H NMR spectrum.

[0046] Fig.31 is 8-fluoro-2-quinolineacetamide in Example 15 13 C NMR spectrum. DETAILED DESCRIPTION

[0047] The preparation method of 2-quinolinecarboxamide of the present invention has the advantages of easy availability of raw materials, fewer reaction steps, mild reaction conditions, recyclable acidic ionic liquid, environmental friendliness, easy operation and high reaction yield.

[0048] The present invention is further described below in conjunction with specific embodiments.

[0049] Example 1: Synthesis of 2-quinolineacetamide

[0050] In a 25 mL reactor, 1-ethyl-3-butyl imidazole hydrogen sulfate ionic liquid (IL1, 0.0125 g, 0.05 mmol), quinoline nitrogen oxide (0.033 g, 0.2 mmol), acetonitrile (0.82 g, 20 mmol) were added, and stirred at 60 ° C for 12 h without solvent. Column chromatography (silica gel, 200-300 mesh; developing solvent, petroleum ether: ethyl acetate) was used to obtain 0.032 g of 2-quinolineacetamide with a yield of 85%.

[0051] The obtained product 2-quinolineacetamide is a white solid.

[0052] H NMR spectroscopy analysis: 1 H NMR (DMSO-d 6 ,400MHz) δ10.81(s,1H),8.30(s,2H),7.88(d,J=4.0Hz,1H),7.79(d,J=8.0Hz,1H),7.70-7.66(m,1H),7.47-7.44(m,1H),2.16(s,3H).

[0053] C NMR spectroscopy analysis: 13 C NMR (DMSO-d 6,100MHz) δ170.3,152.2,146.8,138.6,130.3,128.2,127.3,126.0,125.2,114.7,24.5.

[0054] Example 2: Synthesis of 4-methyl-2-quinolineacetamide

[0055] The operation was the same as in Example 1, and 4-methylquinoline nitrogen oxide was reacted with acetonitrile to obtain 0.032 g of 4-methyl-2-quinolineacetamide with a yield of 80%.

[0056] The obtained product 4-methylquinoline nitrogen oxide is a white solid.

[0057] H NMR spectroscopy analysis: 1 H NMR (DMSO-d 6 ,400MHz)δ10.69(s,1H),8.16(s,1H),7.98(d,J=8.0Hz,1H),7.78(d,J=8.0Hz,1H), 7.68(t,J=8.0,16.0Hz,1H),7.48(t,J=8.0,16.0Hz,1H),2.66(s,3H),2.14(s,3H).

[0058] C NMR spectroscopy analysis: 13 C NMR (DMSO-d 6 ,100MHz) δ170.2,151.9,146.7,146.7,130.1,127.9,126.0,125.1,124.6,114.8,24.5,19.2.

[0059] Example 3: Synthesis of 4-chloro-2-quinolineacetamide

[0060] The operation was the same as in Example 1, and 0.034 g of 4-chloro-2-quinolineacetamide was obtained by the reaction of 4-chloroquinoline nitrogen oxide and acetonitrile. The yield was 77%.

[0061] The obtained product 4-chloroquinoline nitrogen oxide is a white solid.

[0062] H NMR spectroscopy analysis: 1 H NMR (DMSO-d 6 ,400MHz) δ11.02(s,1H),8.48(s,1H),8.08(d,J=8.0Hz,1H),7.86-7.78(m,2H),7.62-7.59(m,1H),2.15(s,3H).

[0063] C NMR spectroscopy analysis: 13 C NMR (DMSO-d6 ,100MHz) δ170.2,151.3,146.9,142.3,131.2,127.5,126.2,123.6,123.2,113.9,24.1.

[0064] Example 4: Synthesis of 4-chloro-6-fluoro-2-quinolineacetamide

[0065] The operation was the same as in Example 1. 4-chloro-6-fluoroquinoline nitrogen oxide was reacted with acetonitrile to obtain 0.035 g of 4-chloro-6-fluoro-2-quinolineacetamide. The yield was 73%.

[0066] The obtained product 4-chloro-6-fluoro-2-quinolineacetamide is a white solid.

[0067] H NMR spectroscopy analysis: 1 H NMR (DMSO-d 6 ,400MHz) δ11.03(s,1H),8.52(s,1H),7.91-7.73(m,3H),2.15(s,3H).

[0068] C NMR spectroscopy analysis: 13 C NMR (DMSO-d 6 ,100MHz)δ170.7,160.0(d, 1 J C-F =244.0Hz),151.40,144.42,142.0(d, 4 J C-F =5.0Hz),130.9(d, 3 J C-F =9.0Hz),129.01,124.3(d, 3 J C-F =10.0Hz),121.6(d, 2 J C-F =25.0Hz),115.15,108.0(d, 2 J C-F =24.0Hz),24.5.

[0069] Example 5: Synthesis of 5-bromo-2-quinolineacetamide

[0070] In a 25mL reactor, 1,3-dibutylimidazole hydrogen sulfate ionic liquid (IL2, 0.0139g, 0.05mmol), 5-bromo-quinoline nitrogen oxide (0.045g, 0.2mmol), acetonitrile (0.041g, 1mmol), tetrahydrofuran (1mL) were added as solvents and stirred at 80°C for 24h. Column chromatography (silica gel, 200-300 mesh; developing solvent, petroleum ether: dichloromethane) was used to obtain 0.042g of 5-bromo-2-quinolineacetamide with a yield of 79%.

[0071] The obtained product 5-bromo-2-quinolineacetamide is a white solid.

[0072] H NMR spectroscopy analysis: 1 H NMR (DMSO-d 6 ,400MHz) δ10.96(s,1H),8.48-8.40(m,2H),7.80(d,J=4.0Hz,2H),7.61(t,J=8.0,16.0Hz,1H),2.17(s,3H).

[0073] C NMR spectroscopy analysis: 13 C NMR (DMSO-d 6 ,100MHz) δ170.6,152.9,147.7,137.5,131.1,129.0,127.7,124.9,121.4,116.2,24.6.

[0074] Example 6: Synthesis of 5-methoxy-2-quinolineacetamide

[0075] The operation was the same as in Example 5, and 5-methoxyquinoline nitrogen oxide was reacted with acetonitrile to obtain 0.036 g of 5-methoxy-2-quinolineacetamide with a yield of 83%.

[0076] The obtained product 5-methoxy-2-quinolineacetamide is a white solid.

[0077] H NMR spectroscopy analysis: 1 H NMR (DMSO-d 6 ,400MHz)δ10.79(s,1H),8.47(d,J=8.0Hz,1H),8.26(d,J=8.0Hz,1H),7.59(t,J=8 .0Hz,1H),7.36(d,J=8.0Hz,1H),6.91(d,J=8.0Hz,1H),3.95(s,3H),2.15(s,3H).

[0078] C NMR spectroscopy analysis: 13 C NMR (DMSO-d 6,100MHz) δ169.8,154.8,152.0,147.3,132.4,130.2,119.1,117.3,113.1,103.5,55.8,24.1.

[0079] Example 7: Synthesis of 6-methyl-2-quinolineacetamide

[0080] In a 25 mL reactor, 1-ethyl-3-butanesulfonic acid imidazolium hydrogen sulfate ionic liquid (IL3, 0.0165 g, 0.05 mmol), 6-methylquinoline nitrogen oxide (0.032 g, 0.2 mmol), acetonitrile (0.041 g, 1 mmol), tetrahydrofuran (1 mL) were added as solvents and stirred at 80°C for 20 h. Column chromatography (silica gel, 200-300 mesh; developing solvent, n-hexane: ethyl acetate) was used to obtain 0.036 g of 6-methyl-2-quinolineacetamide with a yield of 90%.

[0081] The obtained product 6-methyl-2-quinolineacetamide is a white solid.

[0082] H NMR spectroscopy analysis: 1 H NMR (DMSO-d 6 ,400MHz)δ10.74(s,1H),8.25(d,J=12.0Hz,1H),8.16(d,J=8.0Hz,1H),7.68 (d,J=8.0Hz,1H),7.58(s,1H),7.48(d,J=8.0,1H),2.41(s,3H),2.15(s,3H).

[0083] C NMR spectroscopy analysis: 13 C NMR (DMSO-d 6 ,100MHz) δ170.2,151.6,145.2,137.8,134.5,132.3,127.1,126.9,126.0,114.7,24.5,21.3.

[0084] Example 8: Synthesis of 6-fluoro-2-quinolineacetamide

[0085] The operation was the same as in Example 7. 6-Fluoroquinoline N-oxide was reacted with acetonitrile to obtain 0.031 g of 6-fluoro-2-quinolineacetamide. The yield was 75%.

[0086] The obtained product 6-fluoro-2-quinolineacetamide is a white solid.

[0087] H NMR spectroscopy analysis: 1 H NMR (DMSO-d 6,400MHz)δ10.80(s,1H),8.32-8.27(m,2H),7.83-7.80(m,1H),7.69-7.67(m,1H),7.60-7.56(m,1H),2.15(s,3H).

[0088] C NMR spectroscopy analysis: 13 C NMR (DMSO-d 6 ,100MHz)δ170.3,169.2(d, 1 J C-F =241.0Hz),151.8,143.8,138.1(d, 4 J C-F =4.0Hz),129.9(d, 3 J C-F =9.0Hz),126.4(d, 3 J C-F =10.0Hz),120.1(d, 2 J C-F =26.0Hz),115.6,111.4(d, 2 J C-F =22.0Hz),24.5.

[0089] Example 9: Synthesis of 6-chloro-2-quinolineacetamide

[0090] The operation was the same as in Example 7. 6-Chloroquinoline nitrogen oxide was reacted with acetonitrile to obtain 0.034 g of 6-chloro-2-quinolineacetamide. The yield was 78%.

[0091] The obtained product 6-chloro-2-quinolineacetamide is a white solid.

[0092] H NMR spectroscopy analysis: 1 H NMR (DMSO-d 6 ,400MHz) δ10.86(s,1H),8.33-8.27(m,2H),8.00(s,1H),7.79-7.76(m,1H),7.69-7.66(m,1H),2.15(s,3H).

[0093] C NMR spectroscopy analysis: 13 C NMR (DMSO-d 6 ,100MHz) δ170.4,152.6,145.3,138.0,130.8,129.4,129.4,126.9,126.7,115.7,24.5.

[0094] Example 10: Synthesis of 6-bromo-2-quinolineacetamide

[0095] The operation was the same as in Example 7. 6-bromoquinoline nitrogen oxide was reacted with acetonitrile to obtain 0.042 g of 6-bromo-2-quinolineacetamide with a yield of 80%.

[0096] The obtained product 6-bromo-2-quinolineacetamide is a white solid.

[0097] H NMR spectroscopy analysis: 1 H NMR (DMSO-d 6 ,400MHz) δ10.9(s,1H),8.30-8.17(m,3H),7.75(d,J=24.0Hz,2H),2.15(s,3H).

[0098] C NMR spectroscopy analysis: 13 C NMR (DMSO-d 6 ,100MHz) δ170.0,152.2,145.1,137.5,132.9,129.7,129.1,126.9,117.3,115.2,24.1.

[0099] Example 11: Synthesis of 6-methoxy-2-quinolineacetamide

[0100] The operation was the same as in Example 7. 6-methoxyquinoline nitrogen oxide was reacted with acetonitrile to obtain 0.039 g of 6-methoxy-2-quinolineacetamide. The yield was 91%.

[0101] The obtained product 6-methoxy-2-quinolineacetamide is a white solid.

[0102] H NMR spectroscopy analysis: 1 H NMR (DMSO-d 6 ,400MHz) δ10.68(s,1H),8.25-8.18(m,2H),7.69(d,J=8.0Hz,1H),7.34-7.28(m,2H),3.78(s,3H),2.14(s,3H).

[0103] C NMR spectroscopy analysis: 13 C NMR (DMSO-d 6 ,100MHz) δ170.0,156.6,150.3,142.4,137.4,128.8,126.9,122.5,115.0,106.4,55.9,24.4.

[0104] Example 12: Synthesis of 6-nitro-2-quinolineacetamide

[0105] In a 25 mL reactor, 1-butyl-3-butylsulfonic acid imidazole hydrogen sulfate ionic liquid (IL4, 0.0179 g, 0.05 mmol), 6-nitroquinoline nitrogen oxide (0.038 g, 0.2 mmol), acetonitrile (0.041 g, 1 mmol), ethanol (1 mL) were added as solvents and stirred at 80°C for 20 h. Column chromatography (silica gel, 200-300 mesh; developing solvent, n-hexane: ethyl acetate) was used to obtain 0.031 g of 6-nitro-2-quinolineacetamide with a yield of 68%.

[0106] The obtained product 6-nitro-2-quinolineacetamide is a white solid.

[0107] H NMR spectroscopy analysis: 1 H NMR (DMSO-d 6 ,400MHz) δ11.09(s,1H),8.92(d,J=4.0Hz,1H),8.60(d,J=8.0Hz,1H),8.42-8.36(m,2H),7.89(d,J=4.0Hz,1H),2.18(s,3H).

[0108] C NMR spectroscopy analysis: 13 C NMR (DMSO-d 6 ,100MHz) δ170.82,155.00,149.65,143.96,140.88,128.83,125.21,124.64,123.75,116.17,24.67.

[0109] Example 13: Synthesis of 7-methyl-2-quinolineacetamide

[0110] The operation was the same as in Example 12, and 0.034 g of 7-methyl-2-quinolineacetamide was obtained by the reaction of 7-methylquinoline nitrogen oxide and acetonitrile. The yield was 84%.

[0111] The obtained product 7-methyl-2-quinolineacetamide is a white solid.

[0112] H NMR spectroscopy analysis: 1 H NMR (DMSO-d 6 ,400MHz) δ10.74(s,1H),8.25-8.20(m,2H),7.69(d,J=8.0Hz,1H),7.57(s,1H),7.29(d,J=8.0Hz,1H),2.48(s,3H),2.15(s,3H).

[0113] C NMR spectroscopy analysis: 13 C NMR (DMSO-d 6,100MHz) δ170.24,152.20,147.07,140.20,138.25,127.85,127.35,126.35,124.09,113.78,24.52,21.92.

[0114] Example 14: Synthesis of 8-methyl-2-quinolineacetamide

[0115] In a 25 mL reactor, 1,3-dibutylsulfonic acid imidazolium hydrogen sulfate ionic liquid (IL5, 0.0219 g, 0.05 mmol), 8-methylquinoline nitrogen oxide (0.032 g, 0.2 mmol), acetonitrile (0.041 g, 1 mmol), ethyl acetate (1 mL) were added as solvents and stirred at 80°C for 24 h. Column chromatography (silica gel, 200-300 mesh; developing solvent, n-hexane: dichloromethane) was used to obtain 0.025 g of 8-methyl-2-quinolineacetamide with a yield of 80%.

[0116] The obtained product 8-methyl-2-quinolineacetamide is a white solid.

[0117] H NMR spectroscopy analysis: 1 H NMR (DMSO-d 6 ,400MHz) δ10.61(s,1H),8.27(s,2H),7.71(d,J=8.0Hz,1H),7.55(d,J=4.0Hz,1H),7.35(s,1H),2.66(s,3H),2.19(s,3H).

[0118] C NMR spectroscopy analysis: 13 C NMR (DMSO-d 6 ,100MHz) δ170.38,151.19,145.72,138.86,135.14,130.31,126.05,125.94,124.92,114.54,24.64,18.12.

[0119] Example 15: Synthesis of 8-fluoro-2-quinolineacetamide

[0120] The operation was the same as in Example 14, and 8-fluoroquinoline nitrogen oxide was reacted with acetonitrile to obtain 0.023 g of 8-fluoro-2-quinolineacetamide with a yield of 70%.

[0121] The obtained product 8-fluoro-2-quinolineacetamide is a white solid.

[0122] H NMR spectroscopy analysis: 1 H NMR (DMSO-d 6,400MHz) δ11.02(s,1H),8.38(s,2H),7.72(s,1H),7.51-7.44(m,2H),2.15(s,3H).

[0123] C NMR spectroscopy analysis: 13 C NMR (DMSO-d 6 ,100MHz)δ170.6,156.8(d, 1 J C-F =251.0Hz),152.5,138.7,136.6,127.8,125.0(d, 3 J C-F =7.0Hz),124.1,115.7,114.5(d, 2 J C-F =18.0Hz),24.5.

[0124] The specific embodiments of the present invention are described in detail above, but they are only examples, and the present invention is not equivalent to the specific embodiments described above. For those skilled in the art, any equivalent modifications and substitutions made to the present invention are also within the scope of the present invention. Therefore, the equalization changes and modifications made without departing from the spirit and scope of the present invention should be included in the scope of the present invention.

Claims

1. A method for preparing a 2-quinolineamide compound promoted by an acidic ionic liquid, characterized in that: Quinoline N-oxide and acetonitrile were used as starting materials and acidic ionic liquids were used to promote the synthesis of 2-quinoline amide compounds.

2. The method for preparing a 2-quinolineamide compound promoted by an acidic ionic liquid according to claim 1, characterized in that: The acidic ionic liquids are: 1-ethyl-3-butyl imidazolium hydrogen sulfate ionic liquid (IL1), 1,3-dibutyl imidazolium hydrogen sulfate ionic liquid (IL2), 1-ethyl-3-butyl sulfonic acid imidazolium hydrogen sulfate ionic liquid (IL3), 1-butyl-3-butyl sulfonic acid imidazolium hydrogen sulfate ionic liquid (IL4), and 1,3-dibutyl sulfonic acid imidazolium hydrogen sulfate ionic liquid (IL5).

3. The method for preparing a 2-quinolineamide compound promoted by an acidic ionic liquid according to claim 1, wherein the quinoline nitrogen oxide derivative comprises a quinoline nitrogen oxide without a substituent, and a quinoline nitrogen oxide derivative having an electron-donating substituent and an electron-withdrawing substituent at the 4-position, 5-position, 6-position, 7-position and 8-position; The electron donating substituents include: Me and OMe groups; The electron withdrawing substituents include halides and NO2 groups.

4. The method for preparing a 2-quinolineamide compound promoted by an acidic ionic liquid according to claim 1, characterized in that: The preparation method specifically comprises: adding quinoline nitrogen oxide, acetonitrile and acidic ionic liquid into a solution, reacting at a temperature of 30-80° C. for 16-24 hours, and separating the product.

5. The method for preparing a 2-quinolineamide compound promoted by an acidic ionic liquid according to claim 4, characterized in that: The molar ratio of the quinoline nitrogen oxide to the acidic ionic liquid is 1:0.01 to 1:0.

1.

6. The method for preparing a 2-quinolineamide compound promoted by an acidic ionic liquid according to claim 4, characterized in that: The molar ratio of the quinoline nitrogen oxide to acetonitrile is 1:1 to 1:

100.

7. The method for preparing a 2-quinolineamide compound promoted by an acidic ionic liquid according to claim 4, characterized in that: The molar concentration of the quinoline nitrogen oxide is 0.01 mmol / mL to 2 mmol / mL.

8. The method for preparing a 2-quinolineamide compound promoted by an acidic ionic liquid according to claim 4, characterized in that: The solution is one of: N,N-dimethylformamide, dimethyl sulfoxide, tetrahydrofuran, ethylene glycol dimethyl ether, dichloromethane, trifluoroethanol, acetone, toluene, chlorobenzene, 1,4-dioxane, and n-hexane.

9. The method for preparing a 2-quinolineamide compound promoted by an acidic ionic liquid according to claim 1, characterized in that: The product separation is carried out at room temperature, and the method for separating the product includes: column chromatography separation or recrystallization.

10. The method for preparing a 2-quinolineamide compound promoted by an acidic ionic liquid according to claim 4, characterized in that: Water and ethyl acetate or water and dichloromethane are added to the system after the reaction is completed, and then the acidic ionic liquid is separated and recovered for recycling.

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