CN114751856A - Synthetic method of 5-iodine-6-methyl nicotinonitrile - Google Patents
Synthetic method of 5-iodine-6-methyl nicotinonitrile Download PDFInfo
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- CN114751856A CN114751856A CN202210307949.0A CN202210307949A CN114751856A CN 114751856 A CN114751856 A CN 114751856A CN 202210307949 A CN202210307949 A CN 202210307949A CN 114751856 A CN114751856 A CN 114751856A
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- methylnicotinonitrile
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- 238000010189 synthetic method Methods 0.000 title claims abstract description 12
- 229940126062 Compound A Drugs 0.000 claims abstract description 11
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims abstract description 11
- -1 5-iodo-6-methylnicotinonitrile Chemical compound 0.000 claims abstract description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 claims description 18
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 15
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 14
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 12
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 9
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 238000000034 method Methods 0.000 claims 3
- 230000002194 synthesizing effect Effects 0.000 claims 3
- 239000002994 raw material Substances 0.000 abstract description 11
- 238000000297 Sandmeyer reaction Methods 0.000 abstract description 2
- 238000007336 electrophilic substitution reaction Methods 0.000 abstract description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000004537 pulping Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000003674 animal food additive Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Abstract
The invention belongs to the technical field of chemical synthesis, and particularly relates to a synthetic method of 5-iodo-6-methylnicotinonitrile. The compound A is taken as a basic raw material, and the nucleophilic substitution, the electrophilic substitution and the Sandmeyer reaction are sequentially carried out to obtain the 5-iodine-6-methyl nicotinonitrile.
Description
Technical Field
The invention belongs to the technical field of chemical synthesis, and particularly relates to a synthetic method of 5-iodo-6-methylnicotinonitrile.
Background
Nicotinonitrile is a white crystal. Can be sublimed, dissolved in ethanol, diethyl ether, chloroform, benzene and petroleum ether, and slightly dissolved in water. The main application is the intermediate of medicine, food additive, feed additive, pesticide, etc. 5-iodo-6-methylnicotinonitrile is an important derivative of nicotinonitrile.
5-iodo-6-methylnicotinonitrile is an important chemical intermediate, but no synthetic method thereof has been reported so far.
Disclosure of Invention
Aiming at the problems, the invention provides a synthetic method of 5-iodine-6-methylnicotinonitrile, which is simple and convenient to operate and high in yield.
In order to solve the problems, the technical scheme provided by the invention is as follows:
a synthetic method of 5-iodine-6-methyl nicotinonitrile comprises the following steps:
(1) putting the compound A, ammonia water and ethanol into a reactor, heating to 120-125 ℃, setting the pressure to be 1MPa, and reacting to obtain a compound B
(2) Adding compound B, N, N-dimethylformamide and N-iodosuccinimide into a reactor, and reacting to obtain compound C
(3) Adding compound C, DMF and isoamyl nitrite into a reactor, heating to 90 ℃ under the protection of nitrogen, reacting, adding copper powder, and reacting to obtain 5-iodine-6-methyl-nicotinonitrile
Preferably, the ammonia water in the step (1) is 25% by mass, the solid-liquid g/mL ratio of the compound A to the ammonia water is 1:13, and the volume ratio of the ammonia water to the ethanol is 2: 1.
Preferably, in the step (2), the mass ratio of the compound B, N-iodosuccinimide is 7:13, and the solid-liquid g/mL ratio of the compound B, N and the N-dimethylformamide is 7: 110.
Preferably, in the step (3), the mass ratio of the compound C, the isoamyl nitrite and the copper powder is 6: 3-5: 2, and the solid-liquid g/mL ratio of the compound C, DMF is 3: 50.
Has the beneficial effects that:
the compound A is taken as a basic raw material, and the nucleophilic substitution, the electrophilic substitution and the Sandmeyer reaction are sequentially carried out to obtain the 5-iodine-6-methyl nicotinonitrile.
Detailed Description
A synthetic method of 5-iodine-6-methyl nicotinonitrile comprises the following steps:
(1) taking a material according to the solid-liquid g/mL ratio of the compound A to 25% ammonia water of 1:13 and the volume ratio of the ammonia water to ethanol of 2:1, putting the compound A, the ammonia water and the ethanol into a reactor, heating to 120-125 ℃, and reacting under the set pressure of 1MPa to obtain a compound B;
(2) taking materials according to the mass ratio of B, N-iodosuccinimide of 7:13 to B, N and the solid-liquid g/mL ratio of N-dimethylformamide of 7:110, adding B, N, N-dimethylformamide and N-iodosuccinimide into a reactor, and reacting to obtain a compound C;
(3) taking materials according to the mass ratio of the compound C to the isoamyl nitrite to the copper powder of 6: 3-5: 2 and the solid-liquid g/mL ratio of the compound C, DMF of 3:50, adding the compound C, DMF and the isoamyl nitrite into a reactor, carrying out nitrogen protection, heating to 90 ℃, reacting, adding the copper powder, and reacting to obtain the 5-iodo-6-methyl-nicotinonitrile.
Example 1
A synthetic method of 5-iodine-6-methyl nicotinonitrile comprises the following steps:
(1) putting 15g of the compound A, 195mL of ammonia water with the mass fraction of 25% and 97.5mL of ethanol into a reactor, heating to 120 ℃, setting the pressure to be 1MPa, reacting for 3h, detecting by TLC, taking out reaction liquid in the reactor after the raw materials are basically reacted, concentrating the ethanol, filtering, and washing with water to obtain 11.9g of yellow solid, namely the compound B, wherein the yield is 90.9%, and the purity is 96.8%;
(2) Adding 7g of compound B, 110mLN, N-dimethylformamide and 13g N-iodosuccinimide into a reactor, reacting for 15h, detecting by TLC, adding 300mL of water and 200mL of ethyl acetate into the reaction solution after the raw materials react, stirring for 10min, adding diatomite, filtering, separating, continuously extracting the water phase once by 200mL of ethyl acetate, combining the organic phases, concentrating, adding MTBE (20mL), pulping, and filtering to obtain 11.2g of brown solid, namely compound C, wherein the yield is 82.2%, and the purity is 95.2%;
(3) adding 3g of compound C, 50mL of DMF and 1.5g of isoamyl nitrite into a reactor, protecting with nitrogen, heating to 90 ℃, reacting for 2h, adding 1 copper powder, reacting for 4h, detecting by TLC, adding 100mL of water after the raw material reaction is finished, extracting with ethyl acetate (100 mL x 2), combining organic phases, concentrating, stirring, passing through a column, and enabling n-hexane/ethyl acetate to =3% ethyl acetate. Concentration gave 2.2g of white solid, i.e. 5-iodo-6-methyl-nicotinonitrile in 77.8% yield and 99.1% purity.
Nuclear magnetic data of product 1H NMR (400 MHz, DMSO) delta 8.88 (d, J = 2.0Hz, 1H), 8.75 (d, J = 2.0Hz, 1H), 2.72 (s, 3H).
Example 2
A synthetic method of 5-iodine-6-methylnicotinonitrile comprises the following steps:
(1) Putting 15g of the compound A, 195mL of ammonia water with the mass fraction of 25% and 97.5mL of ethanol into a reactor, heating to 123 ℃, setting the pressure to be 1MPa, reacting for 3 hours, detecting by TLC, taking out reaction liquid in the reactor after the raw materials are basically reacted, concentrating the ethanol, filtering, and washing with water to obtain 12.4g of yellow solid, namely the compound B, wherein the yield is 94.7%, and the purity is 97.3%;
(2) adding 7g of compound B, 110mLN, N-dimethylformamide and 13g N-iodosuccinimide into a reactor, reacting for 15h, detecting by TLC, adding 300mL of water and 200mL of ethyl acetate into the reaction solution after the raw materials react, stirring for 10min, adding diatomite, filtering, separating, continuously extracting the water phase once by 200mL of ethyl acetate, combining the organic phases, concentrating, adding MTBE (20mL), pulping, and filtering to obtain 12.6g of brown solid, namely compound C, wherein the yield is 92.5%, and the purity is 97.8%;
(3) adding 3g of compound C, 50mL of DMF and 2g of isoamyl nitrite into a reactor, protecting with nitrogen, heating to 90 ℃, reacting for 2h, adding 1g of copper powder, reacting for 4h, detecting by TLC, adding 100mL of water after the raw material reaction is finished, extracting with ethyl acetate (100 mL x 2), combining organic phases, concentrating, stirring, passing through a column, and enabling n-hexane/ethyl acetate to =3% ethyl acetate. Concentration to obtain 2.8g of white solid, namely 5-iodo-6-methyl-nicotinonitrile with the yield of 99.1% and the purity of 98.6%.
Nuclear magnetic data of product 1H NMR (400 MHz, DMSO) delta 8.88 (d, J = 2.0Hz, 1H), 8.75 (d, J = 2.0Hz, 1H), 2.72 (s, 3H).
Example 3
A synthetic method of 5-iodine-6-methylnicotinonitrile comprises the following steps:
(1) putting 15g of the compound A, 195mL of ammonia water with the mass fraction of 25% and 97.5mL of ethanol into a reactor, heating to 125 ℃, setting the pressure to be 1MPa, reacting for 3h, detecting by TLC, taking out reaction liquid in the reactor after the raw materials are basically reacted, concentrating the ethanol, filtering, and washing with water to obtain 12g of yellow solid, namely the compound B, wherein the yield is 91.7%, and the purity is 95.2%;
(2) adding 7g of compound B, 110mLN, N-dimethylformamide and 13g N-iodosuccinimide into a reactor, reacting for 15h, detecting by TLC, adding 300mL of water and 200mL of ethyl acetate into the reaction solution after the raw materials react, stirring for 10min, adding diatomite, filtering, separating, continuously extracting the water phase once by 200mL of ethyl acetate, combining the organic phases, concentrating, adding MTBE (20mL), pulping, and filtering to obtain 12.3g of brown solid, namely compound C, wherein the yield is 90.3%, and the purity is 96.8%;
(3) adding 3g of compound C, 50mL of DMF and 2.5g of isoamyl nitrite into a reactor, protecting with nitrogen, heating to 90 ℃, reacting for 2h, adding 1g of copper powder, reacting for 4h, detecting by TLC, adding 100mL of water after the reaction of the raw materials is finished, extracting with ethyl acetate (100 mL x 2), combining organic phases, concentrating, stirring, passing through a column, and enabling n-hexane/ethyl acetate to =3% of ethyl acetate. Concentration to obtain 2.5g of white solid, namely the 5-iodine-6-methyl-nicotinonitrile with the yield of 88.5 percent and the purity of 98.2 percent.
Nuclear magnetic data of product 1H NMR (400 MHz, DMSO) delta 8.88 (d, J = 2.0Hz, 1H), 8.75 (d, J = 2.0Hz, 1H), 2.72 (s, 3H).
Claims (4)
1. A synthetic method of 5-iodine-6-methylnicotinonitrile is characterized by comprising the following steps:
(1) putting the compound A, ammonia water and ethanol into a reactor, heating to 120-125 ℃, setting the pressure to be 1MPa, and reacting to obtain a compound B
(2) Adding compound B, N, N-dimethylformamide and N-iodosuccinimide into a reactor, and reacting to obtain compound C
(3) Adding compound C, DMF and isoamyl nitrite into a reactor, heating to 90 ℃ under the protection of nitrogen, reacting, adding copper powder, and reacting to obtain 5-iodine-6-methyl-nicotinonitrile
2. The method for synthesizing 5-iodo-6-methylnicotinonitrile according to claim 1, wherein the ammonia water in the step (1) is 25% by mass, the solid-liquid g/mL ratio of the compound A to the ammonia water is 1:13, and the volume ratio of the ammonia water to the ethanol is 2: 1.
3. The method for synthesizing 5-iodo-6-methylnicotinonitrile according to claim 1, wherein the mass ratio of the compound B, N-iodosuccinimide in the step (2) is 7:13, and the solid-liquid g/mL ratio of the compound B, N and N-dimethylformamide is 7: 110.
4. The method for synthesizing 5-iodo-6-methylnicotinonitrile according to claim 1, wherein in the step (3), the mass ratio of the compound C to the isoamyl nitrite to the copper powder is 6:3 to 5:2, and the solid-liquid g/mL ratio of the compound C, DMF is 3: 50.
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| CN202210307949.0A CN114751856A (en) | 2022-03-27 | 2022-03-27 | Synthetic method of 5-iodine-6-methyl nicotinonitrile |
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| CN202210307949.0A CN114751856A (en) | 2022-03-27 | 2022-03-27 | Synthetic method of 5-iodine-6-methyl nicotinonitrile |
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| CN202210307949.0A Pending CN114751856A (en) | 2022-03-27 | 2022-03-27 | Synthetic method of 5-iodine-6-methyl nicotinonitrile |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103755628A (en) * | 2014-01-27 | 2014-04-30 | 河北科技大学 | Synthetic method for 2-amino-3-iodine-5-pyridyl bromide |
| US9133212B1 (en) * | 2005-06-15 | 2015-09-15 | Vanderbilt University | Inhibitors of hemeprotein-catalyzed lipid peroxidation |
| CN109535138A (en) * | 2017-09-22 | 2019-03-29 | 北京绿人科技有限责任公司 | Triaizine compounds and its application and organic electroluminescence device containing deuterated phenyl |
| WO2021259815A1 (en) * | 2020-06-22 | 2021-12-30 | F. Hoffmann-La Roche Ag | Amidopyrimidone derivatives |
-
2022
- 2022-03-27 CN CN202210307949.0A patent/CN114751856A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9133212B1 (en) * | 2005-06-15 | 2015-09-15 | Vanderbilt University | Inhibitors of hemeprotein-catalyzed lipid peroxidation |
| CN103755628A (en) * | 2014-01-27 | 2014-04-30 | 河北科技大学 | Synthetic method for 2-amino-3-iodine-5-pyridyl bromide |
| CN109535138A (en) * | 2017-09-22 | 2019-03-29 | 北京绿人科技有限责任公司 | Triaizine compounds and its application and organic electroluminescence device containing deuterated phenyl |
| WO2021259815A1 (en) * | 2020-06-22 | 2021-12-30 | F. Hoffmann-La Roche Ag | Amidopyrimidone derivatives |
Non-Patent Citations (4)
| Title |
|---|
| ACS，STN REGISTRY数据库: "RN：1256817-18-1", 《ACS，STN REGISTRY数据库》 * |
| BALU MISAL等: "Sulfated polyborate-H2O assisted tunable activation of N-iodosuccinimide for expeditious mono and diiodination of arenes", 《TETRAHEDRON LETTERS》, vol. 74, pages 153154 * |
| HAO SHEN等: "Remarkable Switch in the Regiochemistry of the Iodination of Anilines by N-Iodosuccinimide: Synthesis of 1, 2-Dichloro-3, 4-diiodobenzene", 《SYNLETT》, vol. 23, no. 2, pages 208 * |
| LIESA RÖDER等: "Flow Hydrodediazoniation of Aromatic Heterocycles", FLOW HYDRODEDIAZONIATION OF AROMATIC HETEROCYCLES, vol. 24, no. 10 * |
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