GB2032922A - Process for the Production of 2- chlorobenzonitrile Derivatives - Google Patents
Process for the Production of 2- chlorobenzonitrile Derivatives Download PDFInfo
- Publication number
- GB2032922A GB2032922A GB7934666A GB7934666A GB2032922A GB 2032922 A GB2032922 A GB 2032922A GB 7934666 A GB7934666 A GB 7934666A GB 7934666 A GB7934666 A GB 7934666A GB 2032922 A GB2032922 A GB 2032922A
- Authority
- GB
- United Kingdom
- Prior art keywords
- parts
- lithium
- chloro
- chloride
- nitrobenzonitrile
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 19
- NHWQMJMIYICNBP-UHFFFAOYSA-N 2-chlorobenzonitrile Chemical class ClC1=CC=CC=C1C#N NHWQMJMIYICNBP-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims abstract description 54
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims abstract description 39
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 13
- 239000000010 aprotic solvent Substances 0.000 claims abstract description 5
- ZHLCARBDIRRRHD-UHFFFAOYSA-N 2-chloro-6-nitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1C#N ZHLCARBDIRRRHD-UHFFFAOYSA-N 0.000 claims description 21
- NJVHJTQSGGRHGP-UHFFFAOYSA-K [Li].[Al+3].[Cl-].[Cl-].[Cl-] Chemical compound [Li].[Al+3].[Cl-].[Cl-].[Cl-] NJVHJTQSGGRHGP-UHFFFAOYSA-K 0.000 claims description 8
- OZKOAADVLVCNFO-UHFFFAOYSA-N 4-chloro-2-nitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1C#N OZKOAADVLVCNFO-UHFFFAOYSA-N 0.000 claims description 3
- RDFDRMZYAXQLRT-UHFFFAOYSA-N 2,3-dichloro-6-nitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(Cl)=C1C#N RDFDRMZYAXQLRT-UHFFFAOYSA-N 0.000 claims description 2
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 33
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 12
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 9
- 238000004817 gas chromatography Methods 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 125000004429 atom Chemical group 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 4
- 150000002642 lithium compounds Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 231100000614 poison Toxicity 0.000 description 3
- 230000007096 poisonous effect Effects 0.000 description 3
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 2
- 229910052808 lithium carbonate Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- QTUXEYXZJLVGOA-UHFFFAOYSA-N 2,3,6-trichlorobenzonitrile Chemical compound ClC1=CC=C(Cl)C(C#N)=C1Cl QTUXEYXZJLVGOA-UHFFFAOYSA-N 0.000 description 1
- GRUHREVRSOOQJG-UHFFFAOYSA-N 2,4-dichlorobenzonitrile Chemical compound ClC1=CC=C(C#N)C(Cl)=C1 GRUHREVRSOOQJG-UHFFFAOYSA-N 0.000 description 1
- MEJVTQKBWPYBFG-UHFFFAOYSA-N 2-amino-6-chlorobenzonitrile Chemical compound NC1=CC=CC(Cl)=C1C#N MEJVTQKBWPYBFG-UHFFFAOYSA-N 0.000 description 1
- DQEOUPUFGJBXFK-UHFFFAOYSA-N 4,5-dichloro-2-nitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC(Cl)=C(Cl)C=C1C#N DQEOUPUFGJBXFK-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 238000000297 Sandmeyer reaction Methods 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- WFIUMNZSBOURNN-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1.N#CC1=CC=CC=C1 WFIUMNZSBOURNN-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- -1 lithium carbonate Chemical class 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
A process for the production of 2- chlorobenzonitrile derivatives of the general formula (I): <IMAGE> (wherein n is 1 or 2) comprises reacting a compound of the general formula (II): <IMAGE> with lithium chloride, or a mixture of lithium chloride and anhydrous aluminium chloride, or lithium aluminium chloride in an aprotic solvent.
Description
SPECIFICATION
Process for the Production of 2-Chlorobenzonitrile Derivatives
This invention relates to a process for producing 2-chlorobenzonitrile derivatives represented by the general formula (I):
(wherein N is a number of 1 or 2) characterized by reacting a compound of the general formula (ill):
(wherein Cl is as defined above) with lithium chloride or a mixture of lithium chloride and anhydrous aluminum chloride or with lithium aluminum chloride in an aprotic solvent.
The compounds represented by the general formula (I) are known as the excellent agricultural chemicals and the intermediates for the preparation of other variety of useful materials.
The following methods are known for the production of 2,6-dichlorobenzonitrile from 2-chloro-6nitrobenzonitrile: 2-chloro-6-nitrobanzonitrile is reduced into 2-chloro-6-aminobenzonitrile and the latter is subjected to a Sandmeyer reaction; and 2-chloro-6-nitrobenzonitrile is treated with chlorine gas (or a mixture thereof with hydrogen chloride gas) or thionyl chloride in a solvent such as dichlorobenzene at high temperature to substitute the nitro group with chlorine. However, the former method is troublesome since it involves many steps such as reduction, diazotization and substitution with chlorine and also releases a large volume of wastes, so that this method is not suited for industrical practice.On the other hand, the latter method uses a material which is poisonous and strongly corrosive and there is also produced nitrogen dioxide gas which is a poisonous and strongly corrosive gas, so that this method has difficulties for practical use.
The process of this invention is capable of producing the object substance with minimized generation of poisonous nitrogen dioxide and very limited release of wastes and with safety by merely reacting a compound of the formula (II) with lithium chloride or a mixture thereof with anhydrous aluminum chloride or with lithium aluminum chloride in an aprotic solvent.
In case of using a mixture of lithium chloride and anhydrous aluminum chloride or lithium aluminum chloride in the process of this invention, the formation of by-products is reduced and the object product can be obtained in a high yield.
It is considered that when a mixture of lithium chloride and anhydrous aluminum chloride is used in this invention, there is formed lithium aluminum chloride with different compositional proportions depending on the mixing ratio of lithium chloride and an hydros aluminum chloride in the reaction system.
A lithium compound, such as lithium carbonate, which can be converted into lithium chloride in the reaction system, may be used in this invention.
Lithium in the lithium compound used in this invention can be easily recovered by mere filtration or in the form of a precipitate by adding an organic solvent such as toluene.
The compounds of the formula (II) used in this invention include 2-chloro-6-nitrobenzonitrile, 4-chloro-2-nitrobenzonitrile, 2,3-dichloro-6-nitrobenzonitrile, 4,5-dichloro-2-nitrobenzonitrile and the like.
The aprotic solvents used in this invention include N,N-dimethylformamide, dimethylsulfoxide,
N,N-dimethylacetamide, hexamethylphosphoramide and N-methylpyrrolidone and the like. Dehydrated solvents are preferable. The amount of the solvent used may vary over a wide range and the preferred amount of the solvent is within the range of 0.5 to 10 times the weight of the compound of the formula (II).
The lithium compound (lithium chloride or lithium aluminum chloride) is used such that the lithium content in the lithium compound is preferably 0.1 to 20 gram atoms, more preferably 0.3 to 3 gram atoms, per mole of the compound of the formula (II).
In case of employing a mixture of lithium chloride and anhydrous aluminum chloride or lithium
aluminum chloride, it is used in such a ratio that the aluminum content is preferably 0.01 to 10 atoms,
more preferably 0.1 to 2 atoms, per atom of lithium.
The reaction of this invention is preferably carried out at a temperature of 1 20 to 2200C, more
preferably at 1 50 to 2000C. The reaction time, although not specifically defined, is usually 0.5 to 20
hours.
The compounds of the formula (I), such as 2,6-dichloro-benzonitrile, obtained according to the
process of this invention can be easily isolated by an ordinary means such as distillation,
recrystallization, etc.
The invention is further described hereinbelow by way of the examples thereof. In the following
descriptions of Examples, all the "parts" are by weight unless otherwise specified.
Example Al
4.55 parts of 2-chloro-6-nitrobenzonitrile, 5.3 parts of lithium chloride and 1 5 parts of N,N
dimethylformamide were refluxed under heating for 2 hours. The reaction temperature was 178-1 7900. The reaction solution was cooled, added with 1 50 parts of toluene, agitated for 30
minutes and then filtered, and the filtrate was analyzed by gas chromatography. It contained 1.25 parts
of 2,6-dichlorobenzonitrile and 2.06 parts of 2-chloro-6-nitrobenzonitrile.
Example A2
4.55 parts of 2-chloro-6-nitrobenzonitrile, 2.12 parts of lithium chloride and 15 parts of N,N
dimethylformamide were refluxed under heating for 2 hours. The reaction temperature was 1 69- 1 700C. The reaction solution was treated similarly to Example Al and analyzed by gas
chromatography, finding 1.27 parts of 2,6-dichlorobenzonitrile and 1.84 parts of 2-chloro-6
nitrobenzonitrile in the reaction solution.
Example A3
4.55 parts of 2-chloro-6-nitrobenzonitrile, 1.06 parts of lithium chloride and 1 5 parts of N,N
dimethylformamide were refluxed under heating for 2 hours. The reaction temperature was 1 63- 1 640C. The reaction solution was treated after the manner of Example A7 and analyzed by gas
chromatography. It contained 1.14 parts of 2,6-dichlorobenzonitrile and 1.96 parts of 2-chloro-6
nitrobenzonitrile.
Example A4
4.55 parts of 2-chloro-6-nitrobenzonitrile, 1.06 parts of lithium chloride and 1 5 parts of N,N
dimethylformamide were refluxed under heating for 3 hours, and the reaction solution was treated
similarly to Example Al and analyzed by gas chromatography, finding 1.29 parts of 2,6
dichlorobenzonitrile and 1.45 parts of 2-chloro-6-nitrobenzonitrile.
Example A5 4.55 parts of 2-chloro-6-nitrobenzonitrile, 5.3 parts of lithium chloride and 5 parts of N,N
dimethylformamide were mixed and reacted at 1800C for 2 hours, and the reaction solution was
treated same as Example Al and then subjected to a gas chromatographic analysis. It contained 1.05
parts of 2,6-dichlorobenzonitrile and 2.46 parts of 2-chloro-6-nitrobenzontrile.
Examples B1--B8 4.55 parts of 2-chloro-6-nitrobenzonitrile and specified quantities (shown in Table 1) of lithium
chloride (LiCI), anhydrous aluminum chloride (AICI3) and N,N-dimethylformamide (DMF) were put into a
100-ml four-necked flask and refluxed under heating at about 1650C for a predetermined period of
time. The reaction solution was cooled, added with 1 50 parts of toluene, agitated for 30 minutes and
then filtered, and the filtrate was analyzed by gas chromatography. The reaction results were as shown
in Table 1 below.
Table 1
Conversion Yield
of 2-chloro- of 2,6- Selectivity
Reaction 6-nitro- dichloro to 2,6-dichloro
Example LiCI AIC13 DMF time benzonitrile henzonitrlle benzonftrlle No. (parts) (parts) (parts) (her) {o/o) {o/O) {a/o) B1 1.06 0.56 15 3 41.0 38.9 94.9
B2 1.06 0.56 15 4 59.6 52.9 88.8
B3 1.06 1.11 15 4 53.7 49.0 91.3
B4 1.06 1.11 15 8 66.0 56.7 85.9
B5 1.06 1.11 10 8 79.7 60.4 75.8
B6 0.53 0.56 15 5 51.5 46.5 90.3
B7 0.53 0.56 15 7 64.9 55.9 86.1
B8 0.22 0.56 15 8 46.5 33.9 72.9
Example B9
4.55 parts of 2-chloro-6-nitrobenzonitrile, 1.06 parts of lithium chloride, 0.53 parts of anhydrous aluminum chloride and 1 5 parts of N,N-dimethylformamide were refluxed under heating in a 100ml four-necked flask. The reaction temperature was 1 640 C. After continuing the reaction for 3 hours, the internal temperature was lowered to 1000C and 0.22 parts of anhydrous aluminum chloride was further added in the reaction solution and again refluxed under heating for 3 hours. Anhydrous aluminum chloride was likewise added three times thereafter, 0.11 part each time, refluxing the mixture under heating for 3 hours after each addition, and the resultant reaction solution was treated similarly to Example B1 and analyzed by gas chromatography, finding 3.28 parts of 2,6dichlorobenzonitrile and 0.08 parts of 2-chloro-6-nitrobenzonitrile.Conversion: 97.9%; yield: 77.1%; selectivity: 78.8%.
Example B10
4.55 parts of 2-chloro-6-nitrobenzonitrile, 1 5 parts of N-methyl-2-pyrrolidone and specified quantities (shown in Table 2) of lithium chloride and anhydrous aluminum chloride were mixed and the mixtures were reacted at various reaction temperatures. Each reaction solution was treated after the manner of Example B1 and analyzed by gas chromatography. The reaction results were as shown in
Table 2 below.
Table 2
Conversion of
2-chloro-6- Yield of Selectivity to
Reaction Reaction nitrobenzo- 2,6-dichloro- 2,6-dichloro
LiCI AICI3 temp. time nitrile benzonitrile benzonitrile (parts) (parts) (0C) (hr) {o/0) { /0) {%) 0.42 1.11 170 12 98.7 89.4 90.6
0.42 1.11 180 6 98.2 89.6 91.2
0.42 1.11 190 3 98.0 88.3 90.1
0.35 1.11 170 14 97.6 86.2 88.4
Example B11
4.55 parts of 2-chloro-6-nitrobenzonitrile, 0.92 parts of lithium carbonate, 2.78 parts of anhydrous aluminum chloride and 15 parts of N-methyl-2-pyrrolidone were put into a 1 00-ml fournecked flask and heated, whereby carbonidoxiode gas was evolved.The mixture was reacted at 1 800C for 2.5 hours and the reaction solution was cooled, added with 100 parts of dichloroethane, agitated for 30 minutes and then filtered, and the filtrate was analyzed by gas chromatography, disclosing conversion of 2-chloro-6-nitrobenzonitrile of 98.0%, yield of 2,6-dichlorobenzonitrile of 85.5% and selectivity to 2,6-dichlorobenzonitrile of 87.2%.
Example B12
4.55 parts of 4-chloro-2-nitrobenzonitrile, 0.42 parts of lithium chloride, 1.11 parts of anhydrous aluminum chloride and 1 5 parts of N-methyl-2-pyrrolidone were reacted at 1 800C for 3 hours after the pattern of Example B1. The reaction solution was added with 100 parts of dichloroethane, agitated for 30 minutes and filtered. Dichloroethane was distilled off from the filtrate and the residue was added with water to precipitate the crude crystals. The crude crystals were recrystallized by using a watermethanol mixed solvent to obtain 3.4 parts of 2,4-dichlorobenzonitrile with purity of 99%. Yield: 79.2%.
Example B13
10.9 parts of 2,3-dichloro-6-nitrobenzontrile, 0.84 parts of lithium chloride, 2.22 parts of anhydrous aluminum chloride and 1 5 parts of N-methyl-2-pyrrolidone were reacted at 1 800C for one hour, and the reaction solution was treated similarly to Example B1 2 to obtain 9.4 parts of 2,3,6trichlorobenzonitrile with purity of almost 100%. Yield: 91.9%.
Example B14
A mixture of 0.84 parts of lithium chloride, 2.22 parts of anhydrous aluminum chloride and 50 parts of toluene was refluxed under heating for 30 minutes to produce lithium aluminum chloride, and the resultant mixture was added with 9.13 parts of 2-chloro-6-nitrobenzonitrile and 20 parts of Nmethyl-2-pyrrolidone. After distilling off toluene, the mixture was reacted at 1 800C for 8 hours. The reaction solution was treated in the same way as Example B1 and analyzed by gas chromatography, obtaining the following results: Conversion of 2-chloro-6-nitrobenzonitrile: 98.0%; Yield of 2,6dichlorobenzonitrile: 87.3%; Selectivity to 2,6-dichloro-benzonitrile: 89.1%.
Claims (6)
1. A process for producing 2-chlorobenzonitrile derivatives of the general formula (I):
(wherein N is 1 or 2), which process comprises reacting a compound of the general formula (ill):
(wherein n is as defined above) with lithium chloride, a mixture of lithium chloride and anhydrous aluminum chloride, or lithium aluminum chloride in an aprotic solvent.
2. A process according to claim 1, wherein the compound of formula (II) is 2-chloro-6nitrobenzonitrile.
3. A process according to claim 1, wherein the compound of formula (II) is 4-chloro-2nitrobenzonitrile.
4. A process according to claim 1, wherein the compound of formula (II) is 2,3-dichloro-6nitrobenzonitrile.
5. A process according to claim 1, wherein the compound of formula (II) is 4,5-dichloro-2dinitrobenzonitrile.
6. A process according to claim 1 substantially as described in any one of the Examples.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12487578A JPS5551047A (en) | 1978-10-11 | 1978-10-11 | Preparation of 2,6-dichlorobenzonitrile |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2032922A true GB2032922A (en) | 1980-05-14 |
| GB2032922B GB2032922B (en) | 1982-12-22 |
Family
ID=14896248
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7934666A Expired GB2032922B (en) | 1978-10-11 | 1979-10-05 | Process for the production of 2-chloro-benzonitrile derivatives |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS5551047A (en) |
| GB (1) | GB2032922B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7482125B2 (en) * | 2018-11-16 | 2024-05-13 | アリスタ ライフサイエンス インコーポレイテッド | Process for the preparation of 2,6-dichlorobenzonitrile |
-
1978
- 1978-10-11 JP JP12487578A patent/JPS5551047A/en active Granted
-
1979
- 1979-10-05 GB GB7934666A patent/GB2032922B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB2032922B (en) | 1982-12-22 |
| JPS5551047A (en) | 1980-04-14 |
| JPS614390B2 (en) | 1986-02-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4225534A (en) | Process for the production of 2-chlorobenzonitrile derivatives | |
| US4769493A (en) | Process for producing tetrafluorophthalic acid | |
| US4788298A (en) | Process for the preparation of coumarin compounds | |
| GB2032922A (en) | Process for the Production of 2- chlorobenzonitrile Derivatives | |
| CA2233807C (en) | Chlorination of substituted alkenes using tricholorisocyanuric acid | |
| US4394527A (en) | Method for the liquid phase oxidative fluorination of aromatic compounds | |
| US3984487A (en) | Preparation of petachloronitrobenzene | |
| EP1065198B1 (en) | Process for the production of Malononitrile | |
| EP0259663B1 (en) | Process for producing tetrafluorophihalic acid | |
| JPH072751A (en) | 2,3-difluoro-6-nitrobenzonitrile, 2-chloro-5,6- difluorobenzonitrile (2,3-difluoro-6-chlorobenzonitrile), their production and method of using them to produce 2,3,6-trifluorobenzoic acid | |
| Margaretha et al. | Synthesis of imines of. alpha.,. beta.-acetylenic ketones | |
| US4766243A (en) | Electrophilic fluorination of aromatic compounds | |
| KR940000062B1 (en) | Process for preparation of acylcyanide in medium anhydride | |
| HU209738B (en) | Process for the preparation and isolation of alkyl-3-chloroanthranilates | |
| US4021443A (en) | Perchlorodiazafulvene | |
| Bell et al. | Reaction of ketone enolates with 2, 4-dichloropyrimidine. A novel pyrimidine to pyridine interconversion | |
| US4417081A (en) | Selective 2-chlorination of meta-dihalobenzenes | |
| US4074052A (en) | Process for preparation of isocyanuric acid triesters | |
| Porwisiak et al. | Polyhaloaromatics. Part V. Synthesis of poly-and perfluoro-1, 3, 5, 7-tetrahydrobenzo [1, 2-c: 4, 5-c′] difurans | |
| JP3903291B2 (en) | Process for producing 2,3,6,7,10,11-hexaalkoxytriphenylenes | |
| US4013674A (en) | N-(1,2,2,2-tetrachloroethyl)-formimide-chloride for synthesizing trichlorothiazole | |
| JP2540167B2 (en) | Method for producing maleimide | |
| KR940019673A (en) | Process for preparing phenylbenzamide derivative | |
| KR940005021B1 (en) | Method for preparing 5-chloro-2,4,6-trifluoropyrimidine | |
| JP3225361B2 (en) | Method for producing aromatic fluorine compound and fluorine-containing benzenesulfinic acid derivative as raw material |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19921005 |