CN114436974A - Synthesis method of 7-bromo-6-chloro-4 (3H) -quinazolinone - Google Patents
Synthesis method of 7-bromo-6-chloro-4 (3H) -quinazolinone Download PDFInfo
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- CN114436974A CN114436974A CN202210143971.6A CN202210143971A CN114436974A CN 114436974 A CN114436974 A CN 114436974A CN 202210143971 A CN202210143971 A CN 202210143971A CN 114436974 A CN114436974 A CN 114436974A
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- chloro
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- quinazolinone
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- RFCXXKWROOFQSI-UHFFFAOYSA-N 7-bromo-6-chloro-1h-quinazolin-4-one Chemical compound N1=CNC(=O)C2=C1C=C(Br)C(Cl)=C2 RFCXXKWROOFQSI-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 238000001308 synthesis method Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims abstract description 13
- BHWZSQKCDWJPSY-UHFFFAOYSA-N 2,4-dibromo-5-chlorobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=C(Br)C=C1Br BHWZSQKCDWJPSY-UHFFFAOYSA-N 0.000 claims abstract description 7
- XPOLVIIHTDKJRY-UHFFFAOYSA-N acetic acid;methanimidamide Chemical compound NC=N.CC(O)=O XPOLVIIHTDKJRY-UHFFFAOYSA-N 0.000 claims abstract description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 12
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 12
- 238000000967 suction filtration Methods 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 7
- 230000002194 synthesizing effect Effects 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 239000012065 filter cake Substances 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 6
- 150000007529 inorganic bases Chemical class 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 4
- 229940045803 cuprous chloride Drugs 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 238000010189 synthetic method Methods 0.000 claims description 4
- 229910021589 Copper(I) bromide Inorganic materials 0.000 claims description 3
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 claims description 3
- 238000004321 preservation Methods 0.000 claims description 3
- 235000009518 sodium iodide Nutrition 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 2
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 claims description 2
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 claims description 2
- 229940112669 cuprous oxide Drugs 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 2
- 230000001105 regulatory effect Effects 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims 1
- 229940079593 drug Drugs 0.000 abstract description 5
- 239000003814 drug Substances 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- SJUWEPZBTXEUMU-LDXVYITESA-N 7-bromo-6-chloro-3-[3-[(2s,3r)-3-hydroxypiperidin-2-yl]-2-oxopropyl]quinazolin-4-one;hydrobromide Chemical compound Br.O[C@@H]1CCCN[C@H]1CC(=O)CN1C(=O)C2=CC(Cl)=C(Br)C=C2N=C1 SJUWEPZBTXEUMU-LDXVYITESA-N 0.000 abstract description 2
- 230000001165 anti-coccidial effect Effects 0.000 abstract description 2
- 206010059866 Drug resistance Diseases 0.000 abstract 1
- 231100000053 low toxicity Toxicity 0.000 abstract 1
- 239000000047 product Substances 0.000 description 3
- QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical class C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 description 2
- TUDNMLBIHIWVJM-UHFFFAOYSA-N 2-amino-5-bromo-4-chlorobenzoic acid Chemical compound NC1=CC(Cl)=C(Br)C=C1C(O)=O TUDNMLBIHIWVJM-UHFFFAOYSA-N 0.000 description 2
- HVPQMLZLINVIHW-UHFFFAOYSA-N 6-bromo-1h-indole-2,3-dione Chemical compound BrC1=CC=C2C(=O)C(=O)NC2=C1 HVPQMLZLINVIHW-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- DHYHYLGCQVVLOQ-UHFFFAOYSA-N 3-bromoaniline Chemical compound NC1=CC=CC(Br)=C1 DHYHYLGCQVVLOQ-UHFFFAOYSA-N 0.000 description 1
- ITRAKBJPMLKWIW-UHFFFAOYSA-N 4-Bromoisatin Chemical compound BrC1=CC=CC2=C1C(=O)C(=O)N2 ITRAKBJPMLKWIW-UHFFFAOYSA-N 0.000 description 1
- VILDUFSHBWCWIF-UHFFFAOYSA-N 6-bromo-5-chloro-1h-indole-2,3-dione Chemical compound C1=C(Br)C(Cl)=CC2=C1NC(=O)C2=O VILDUFSHBWCWIF-UHFFFAOYSA-N 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- -1 nitrogen-containing heterocyclic compounds Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 239000000273 veterinary drug Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
Abstract
The invention discloses a method for preparing 7-bromo-6-chloro-4 (3H) -quinazolinone, which is a key intermediate of anticoccidial drug halofuginone hydrobromide with the advantages of broad spectrum, high efficiency, safety, low toxicity and no cross drug resistance. The method takes 2, 4-dibromo-5-chlorobenzoic acid as a raw material to react with formamidine acetate in one step to prepare the product 7-bromo-6-chloro-4 (3H) -quinazolinone. The invention has the advantages of simple synthesis process, low production cost, few steps, high total yield and little pollution, and is suitable for industrial mass production.
Description
Technical Field
The invention relates to the technical field of drug synthesis, in particular to a synthesis method of 7-bromo-6-chloro-4 (3H) -quinazolinone.
Background
The 4(3H) -quinazolinone compounds are important nitrogen-containing heterocyclic compounds, have wide pharmacological activities, comprise antimicrobial, antitumor, anti-inflammatory, anticonvulsant and the like, are used as important intermediates, and are widely applied to the fields of medicines, pesticides, veterinary medicines and the like. 7-bromo-6-chloro-4 (3H) -quinazolinone (17518-98-8) belongs to 4(3H) -quinazolinone compounds, and has a chemical formula C8H4BrClN2O, is a key intermediate for synthesizing the anticoccidial drug halofuginone hydrobromide, the total global demand in the field of veterinary drugs can reach 20 tons, and the most common synthetic method is that 5-bromo-4-chloro-2-aminobenzoic acid is used as a raw material and is subjected to condensation reaction with formamide in DMF, and the reaction equation is as follows:
the raw material 5-bromo-4-chloro-2-aminobenzoic acid is prepared by taking m-bromoaniline as a starting material, performing Sandmoer and condensation two-step reaction to obtain 6-bromoisatin, chlorinating by sulfonyl chloride to obtain 5-chloro-6-bromoisatin, and finally reacting with hydrogen peroxide under an alkaline condition. However, this step of condensation produces the isomer 4-bromoisatin, which adds significantly to the cost of the starting material.
Disclosure of Invention
The invention aims to provide a novel method for preparing 7-bromo-6-chloro-4 (3H) -quinazolinone, which avoids using high-cost raw materials in the old method and meets the requirement of industrial production.
The aim of the invention is achieved by the following technical measures:
mixing 2, 4-dibromo-5-chlorobenzoic acid, a catalyst 1, a catalyst 2, inorganic base, formamidine acetate and a solvent, and reacting for a certain time under the condition of heat preservation; after the reaction is stopped, cooling, performing suction filtration, recovering filtrate, transferring a filter cake into water, adding activated carbon, stirring for a certain time, and performing suction filtration; and (3) regulating the pH value of the filtrate to 2-3 by using hydrochloric acid, separating out a large amount of solids, carrying out suction filtration, and drying a filter cake to obtain the 7-bromo-6-chloro-4 (3H) -quinazolinone.
Wherein the synthetic reaction formula of the 7-bromo-6-chloro-4 (3H) -quinazolinone is as follows:
further, the mass ratio of the 2, 4-dibromo-5-chlorobenzoic acid, the catalyst 1, the catalyst 2, the inorganic base, the formamidine acetate, the solvent, the water, the activated carbon and the hydrochloric acid is 1 (0.02-0.05), (0.4-3.1), (0.35-0.66), (6-8), (8-10), (0.03-0.05) and (0.35-0.45).
Further, the catalyst 1 is cuprous chloride, cuprous bromide or cuprous oxide, preferably cuprous chloride.
Further, the catalyst 2 is sodium iodide or potassium iodide, preferably potassium iodide.
Further, the inorganic base is sodium carbonate, potassium carbonate, cesium carbonate, sodium hydroxide or potassium hydroxide, preferably potassium hydroxide.
Further, the solvent is acetonitrile, propionitrile, methyltetrahydrofuran, 1, 4-dioxane, DMF or N-methylpyrrolidone, preferably acetonitrile.
The method for preparing 7-bromo-6-chloro-4 (3H) -quinazolinone has the following advantages:
the synthesis steps are only one step, and the yield is high.
The solvent in the reaction can be recovered and reused.
Low raw material cost and little pollution, and is suitable for industrial mass production.
Drawings
FIG. 1 is an infrared spectrum (IR) of the 7-bromo-6-chloro-4 (3H) -quinazolinone product synthesized in example 1
FIG. 2 is a Mass Spectrum (MS) of the 7-bromo-6-chloro-4 (3H) -quinazolinone product synthesized in example 1
FIG. 3 is a NMR spectrum of 7-bromo-6-chloro-4 (3H) -quinazolinone product synthesized in example 1: (1HNMR)
Detailed Description
The following examples are presented to enable one of ordinary skill in the art to more fully understand the present invention and are not intended to limit the invention in any way.
Example 1
A synthetic method of 7-bromo-6-chloro-4 (3H) -quinazolinone comprises the following specific operation steps:
100g of 2, 4-dibromo-5-chlorobenzoic acid, 3g of cuprous chloride, 3g of potassium iodide, 55g of potassium hydroxide, 40g of formamidine acetate and 700g of acetonitrile are sequentially added into a reaction bottle, heated under reflux, stirred and reacted for 18 hours, and the reaction is finished. Cooling the reaction system to 20-30 ℃; performing suction filtration, adding the filter cake into 900g of water, adding 4g of active carbon, and stirring for 2 hours; and (3) carrying out suction filtration, adjusting the pH value of the filtrate to 2-3 by using hydrochloric acid, separating out a solid, carrying out suction filtration, and drying at 100-110 ℃ to obtain a white solid 7-bromo-6-chloro-4 (3H) -quinazolinone (71.5g, wherein the yield is 86.7%).
Example 2
A synthetic method of 7-bromo-6-chloro-4 (3H) -quinazolinone comprises the following specific operation steps:
100g of 2, 4-dibromo-5-chlorobenzoic acid, 5g of cuprous bromide, 5g of sodium iodide, 50g of sodium hydroxide, 40g of formamidine acetate and 700g of acetonitrile are sequentially added into a reaction bottle, heated under reflux, stirred and reacted for 20 hours, and the reaction is finished. Cooling the reaction system to 20-30 ℃, carrying out suction filtration, adding a filter cake into 900g of water, adding 4g of activated carbon, and stirring for 2 hours; and (3) performing suction filtration, adjusting the pH of the filtrate to 2-3 by using hydrochloric acid, precipitating a solid, performing suction filtration, and drying at 100-110 ℃ to obtain a white solid 7-bromo-6-chloro-4 (3H) -quinazolinone (68.6g, wherein the yield is 83.2%).
While the invention has been described in detail by way of the general description and the specific examples, it will be apparent to those skilled in the art that various modifications and improvements can be made without departing from the spirit of the invention.
Claims (8)
1. A synthetic method of 7-bromo-6-chloro-4 (3H) -quinazolinone is characterized by comprising the following steps:
mixing 2, 4-dibromo-5-chlorobenzoic acid, a catalyst 1, a catalyst 2, inorganic base, formamidine acetate and a solvent, and reacting for a certain time under the condition of heat preservation;
after the reaction is stopped, cooling, performing suction filtration, recovering filtrate, transferring a filter cake into water, adding activated carbon, stirring for a certain time, and performing suction filtration; and (3) regulating the pH value of the filtrate to 2-3 by using hydrochloric acid, separating out a large amount of solids, performing suction filtration, and drying a filter cake at the temperature of 100-.
Wherein the synthetic reaction formula of the 7-bromo-6-chloro-4 (3H) -quinazolinone is as follows:
2. the method of claim 1, wherein the mass ratio of 2, 4-dibromo-5-chlorobenzoic acid to catalyst 1 to catalyst 2 to inorganic base to formamidine acetate to solvent to water to activated carbon to hydrochloric acid is 1 (0.02-0.05): 0.4-3.1): 0.35-0.66): 6-8): 8-10): 0.03-0.05): 0.35-0.45.
3. The method for synthesizing 7-bromo-6-chloro-4 (3H) -quinazolinone according to claim 1, characterized in that said catalyst 1 is cuprous chloride, cuprous bromide or cuprous oxide.
4. The method for synthesizing 7-bromo-6-chloro-4 (3H) -quinazolinone according to claim 1, characterized in that said catalyst 2 is sodium iodide or potassium iodide.
5. The method for synthesizing 7-bromo-6-chloro-4 (3H) -quinazolinone according to claim 1, characterized in that said inorganic base is sodium carbonate, potassium carbonate, cesium carbonate, sodium hydroxide or potassium hydroxide.
6. The method for synthesizing 7-bromo-6-chloro-4 (3H) -quinazolinone according to claim 1, characterized in that said solvent is acetonitrile, propionitrile, methyl tetrahydrofuran, 1, 4-dioxane, DMF or N-methylpyrrolidone, etc.
7. The method for synthesizing 7-bromo-6-chloro-4 (3H) -quinazolinone according to claim 1, characterized in that the temperature of the heat preservation reaction is 76-120 ℃.
8. The method for synthesizing 7-bromo-6-chloro-4 (3H) -quinazolinone according to claim 1, characterized in that the reaction time is 12-20 hours.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202210143971.6A CN114436974A (en) | 2022-02-17 | 2022-02-17 | Synthesis method of 7-bromo-6-chloro-4 (3H) -quinazolinone |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116008435A (en) * | 2023-02-03 | 2023-04-25 | 沈阳感光化工研究院有限公司 | Method for measuring content of 2, 4-dibromo-5-chlorobenzoic acid by high performance liquid chromatography |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102351790A (en) * | 2011-09-15 | 2012-02-15 | 南昌大学 | Method for synthesizing 7-bromo-6-chloro-4-quinazolinone |
| CN112409272A (en) * | 2020-11-26 | 2021-02-26 | 河北美荷药业有限公司 | Preparation method and application of 6-chloro-7-bromo-4 (3H) -quinazolinone |
| CN112778218A (en) * | 2021-01-08 | 2021-05-11 | 湖北工程学院 | Method for preparing quinazolinone and derivative thereof by using chitosan loaded copper catalyst |
| CN113754594A (en) * | 2021-09-16 | 2021-12-07 | 中国药科大学 | Quinazolinone compound or pharmaceutically acceptable salt and isomer thereof, preparation method, pharmaceutical composition and application thereof |
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2022
- 2022-02-17 CN CN202210143971.6A patent/CN114436974A/en not_active Withdrawn
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102351790A (en) * | 2011-09-15 | 2012-02-15 | 南昌大学 | Method for synthesizing 7-bromo-6-chloro-4-quinazolinone |
| CN112409272A (en) * | 2020-11-26 | 2021-02-26 | 河北美荷药业有限公司 | Preparation method and application of 6-chloro-7-bromo-4 (3H) -quinazolinone |
| CN112778218A (en) * | 2021-01-08 | 2021-05-11 | 湖北工程学院 | Method for preparing quinazolinone and derivative thereof by using chitosan loaded copper catalyst |
| CN113754594A (en) * | 2021-09-16 | 2021-12-07 | 中国药科大学 | Quinazolinone compound or pharmaceutically acceptable salt and isomer thereof, preparation method, pharmaceutical composition and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| LIU XIAOWEI等: "A Simple and Efficient Approach to Quinazolinones under Mild Copper-Catalyzed Conditions", ANGEW. CHEM. INT. ED., no. 48, pages 348 - 351 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116008435A (en) * | 2023-02-03 | 2023-04-25 | 沈阳感光化工研究院有限公司 | Method for measuring content of 2, 4-dibromo-5-chlorobenzoic acid by high performance liquid chromatography |
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